| Identification | More | [Name]
BOC-L-Proline | [CAS]
15761-39-4 | [Synonyms]
1,2-PYRROLIDINEDICARBOXYLIC ACID, 1-(1,1-DIMETHYLETHYL) ESTER, (2S)-
BOC-L-PRO
BOC-L-PROLINE
BOC-L-PROLINE-OH
BOC-L-PRO-OH
BOC-PRO
BOC-PROLINE
BOC-PRO-OH
BOC-PYRD(2)-OH
N-ALPHA-T-BOC-L-PROLINE
N-ALPHA-T-BUTOXYCARBONYL-L-PROLINE
N-ALPHA-T-BUTOXYCARBONYL-L-PYRROLIDINE-2-CARBOXYLIC ACID
n-alpha-tert-boc-l-proline
N-ALPHA-TERT-BUTYLOXYCARBONYL-L-PROLINE
N-BOC-L-PROLINE
N-T-BOC-L-PROLINE
N-T-BUTOXYCARBONYL-L-PROLINE
N-(TERT-BUTOXYCARBONYL)-L-PROILNE
N-(TERT-BUTOXYCARBONYL)-L-PROLINE
N-(TERT-BUTYLOXYCARBONYL)-L-PROLINE | [EINECS(EC#)]
239-848-3 | [Molecular Formula]
C10H17NO4 | [MDL Number]
MFCD00037324 | [Molecular Weight]
215.25 | [MOL File]
15761-39-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white microcrystalline powder | [Melting point ]
133-135 °C(lit.)
| [alpha ]
-60.5 º (c=1, HAc) | [Boiling point ]
355.52°C (rough estimate) | [density ]
1.1835 (rough estimate) | [refractive index ]
-60 ° (C=2, AcOH) | [storage temp. ]
Store at RT. | [solubility ]
Soluble in acetic acid. | [form ]
Crystals or Crystalline Powder | [pka]
4.01±0.20(Predicted) | [color ]
White | [Optical Rotation]
[α]20/D 61±2°, c = 2% in acetic acid | [Detection Methods]
T,NMR,Rotation | [BRN ]
15828 | [Major Application]
peptide synthesis | [InChI]
1S/C10H17NO4/c1-10(2,3)15-9(14)11-6-4-5-7(11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)/t7-/m0/s1 | [InChIKey]
ZQEBQGAAWMOMAI-ZETCQYMHSA-N | [SMILES]
CC(C)(C)OC(=O)N1CCC[C@H]1C(O)=O | [CAS DataBase Reference]
15761-39-4(CAS DataBase Reference) | [EPA Substance Registry System]
15761-39-4(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Description]
N-Boc-L-proline is a synthetic intermediate.1,2 It has been used in the synthesis of enantioselective catalysts for aldol reactions and hepatitis C virus (HCV) NS5A inhibitors. | [Chemical Properties]
White to off-white microcrystalline powder | [Uses]
N-Boc-L-proline is used as an intermediate in organic synthesis. It is also used to prepare daclatasvir, which inhibits the hepatitis C virus (HCV) non-structural 5A (NS5A) protein. Further, it is used as a drug in the treatment of hepatitis C virus (HCV). | [Preparation]
Triethylamine (16.5 mL, 0.12 mmol) was added dropwise over a period of 10 min to a stirred, ice-cold suspension of l-proline (10.0 g, 8.7 mmol) in dichloromethane (200 mL) in a 500-mL three-necked, round-bottomed flask. A solution of Boc2O (28.3 g, 0.13 mmol) in dichloromethane (100 mL) was then added over a period of 10 min and the mixture was stirred for 2.5 h. Thereafter, 10% aqueous citric acid (50 mL) was added, and the dichloromethane layer was washed with saturated brine (2×50 mL) and with water (50 mL). After drying the organic phase over magnesium sulfate, the solvent was evaporated and the residue was taken up in hot ethyl acetate. Dilution of this solution with hexane gave the product, N-tertbutoxycarbonyl- L-proline (17.8 g, 95%); mp 138–140℃; TLC (silica gel): Rf=0:36 (EtOAc/MeOH, 1:1). | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [References]
[1] ALBRECHT BERKESSEL Johann L Burkhard Koch. Proline-Derived N-Sulfonylcarboxamides: Readily Available, Highly Enantioselective and Versatile Catalysts for Direct Aldol Reactions[J]. Advanced Synthesis & Catalysis, 2004, 346 9-10: 1141-1146. DOI: 10.1002/adsc.200404126
[2] JUNXING SHI . Synthesis and biological evaluation of new potent and selective HCV NS5A inhibitors[J]. Bioorganic & Medicinal Chemistry Letters, 2012, 22 10: Pages 3488-3491. DOI: 10.1016/j.bmcl.2012.03.089 |
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Alfa Aesar
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Energy Chemical
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