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1448189-80-7

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1448189-80-7 Structure

1448189-80-7 Structure
IdentificationBack Directory
[Name]

(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride
[CAS]

1448189-80-7
[Synonyms]

ULM-1
141003
CS-2718
ULM-1 HCl
MDK7526 HCl
VHL Ligand 1
MDK-7526;ULM-1
VH032 amine HCl
ULM-1(MDK7526HCL)
Protein degrader 1
PROTAC-VHL-Ligand 1
VHL Ligand 1 HCl salt
ULM-1HCl (MDK7526 HCl
Protein degrader 1 HCl)
VH032-NH2 hydrochloride
VHL ligand 1 hydrochlorid
(S,R,S)-AHPC hydrochloride
MDK7526(Protein degrader 1)
VHL Ligand 1 (hydrochloride)
VH032 desacetyl Hydrochloride
Degradation Inducing Moiety A
PROTAC-VHL-ligand hydrochloride
(S,R,S)-AHPC hydrochloride >=97%
Protein degrader 1 (hydrochloride)
(2S,4R)-1-((S)-2-Amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine
(4R)-3-Methyl-L-valyl-4-hydroxy-N-[[4-(4-methyl-5-thiazolyl)phenyl]methyl]-L-prolinamide hydrochloride
(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride
(2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide hydrochloride
(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride ISO 9001：2015 REACH
PROTEIN DEGRADER 1 HYDROCHLORIDE; MDK7526 HCL; MDK7526; MDK-7526; MDK 7526; VHL LIGAND 1; ULM-1; VH032 DESACETYL HYDROCHLORIDE; VH032 AMINE HCL; DEGRADATION INDUCING MOIETY A;
[EINECS(EC#)]

604-604-1
[Molecular Formula]

C22H31ClN4O3S
[MOL File]

1448189-80-7.mol
[Molecular Weight]

467.03
Chemical PropertiesBack Directory
[storage temp. ]

2-8°C
[solubility ]

DMF: 20 mg/ml; DMSO: 20 mg/ml; Ethanol: 20 mg/ml; PBS (pH 7.2): 10 mg/ml
[form ]

A crystalline solid
[color ]

White to yellow
[Appearance]

yellow-brown powder
[InChIKey]

JYRTWGCWUBURGU-XIMRXPCLNA-N
[SMILES]

C([C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)C(C)(C)C)(=O)NCC1C=CC(C2=C(N=CS2)C)=CC=1.Cl |&1:1,3,9,r|
Safety DataBack Directory
[WGK Germany ]

WGK 3
[HS Code ]

2934100090
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

VHL ligand 1 is a building block in the synthesis of proteolysis-targeting chimera technologies (PROTACs). It is the von Hippel-Lindau (VHL) E3 ligase binding portion of some VHL-based PROTACs, including BET PROTAC MZ1 (Item No. 21622).
[Uses]

(S,R,S)-AHPC (HCl salt) is a ligand used in the recruitment of the von Hippel-Lindau (VHL) protein for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This (S,R,S) conformation is the active variant, and (S,S,S) is the inactive derivative (cat#901487) used as a negative control.
[reaction suitability]

reagent type: ligand
[Synthesis]

tert-butyl ((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate

1448189-98-7

(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride

1448189-80-7

Step 4: Synthesis of (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride (ULM-1) To a stirred solution of tert-butyl N-[(2S)-1-[(2S,4R)-4-hydroxy-2-({[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}carbamoyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate (12 g, 22.61 mmol) in dioxane (20 mL) at room temperature was added to a dioxane solution of hydrogen chloride (4N, 80 mL). The reaction mixture was stirred at room temperature for 2 h. LC-MS monitoring showed formation of the target product. The precipitated solid was collected by filtration to give ULM-1 in 48% yield as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 9.84-9.82 (s, 1H), 7.58-7.54 (m, 4H), 4.71-4.41 (m, 4H), 4.13-4.08 (m, 1H), 3.86-3.71 (m, 2H), 3.36 (s, 1H), 2.60-2.58 (s, 3H), 2.35-2.07 (m, 2H), 1.19-1.12 (m, 9H). LC-MS (ES+): m/z 431.11 [MH+], tR = 0.73 min (run time 2.0 min).

[IC 50]

VHL
[References]

[1] Patent: WO2016/118666, 2016, A1. Location in patent: Paragraph 0398; 0399; 0411; 0412
[2] Patent: US2017/8904, 2017, A1. Location in patent: Paragraph 0376; 0382
[3] Patent: US2017/281784, 2017, A1. Location in patent: Paragraph 0191; 0197
[4] Patent: US2018/125821, 2018, A1
[5] Patent: WO2014/108452, 2014, A1. Location in patent: Page/Page column 50
Spectrum DetailBack Directory
[Spectrum Detail]

(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride(1448189-80-7)1HNMR
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