| Identification | More | [Name]
D-1-N-Boc-prolinamide | [CAS]
35150-07-3 | [Synonyms]
1-BOC-L-PROLINAMIDE
BOC-L-PROLINAMIDE
BOC-L-PROLINE AMIDE
BOC-L-PRO-NH2
BOC-PRO-NH2
BOC-PYRD(2)-NH2
L-1-N-BOC-PROLIDINAMIDE
(L)-1-N-BOC-PROLINAMIDE
N-ALPHA-T-BUTOXYCARBONYL-L-PROLINE AMIDE
N-ALPHA-T-BUTOXYCARBONYL-L-PYRROLIDINE-2-CARBOXYLIC ACID AMIDE
N-ALPHA-T-BUTYLOXYCARBONYL-L-PROLINE AMIDE
N-ALPHA-TERT-BUTYLOXYCARBONYL-L-PROLINE AMIDE
N-TERT-BUTOXYCARBONYL-L-PROLINE AMIDE
N-(TERT-BUTOXYCARBONYL)PROLINE AMIDE
(S)-2-(AMINOCARBONYL)-1-PYRROLIDINECARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER
(S)-2-CARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
DL-1-BOC-PROLINAMIDE
Boc-D-Prolinamide
D-1-N-Boc-prolinamide
tert-Butyl (2R)-2-carbamoylpyrrolidine-1-carboxylate | [EINECS(EC#)]
626-262-1 | [Molecular Formula]
C10H18N2O3 | [MDL Number]
MFCD00190827 | [Molecular Weight]
214.26 | [MOL File]
35150-07-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
104-108 °C | [Boiling point ]
370.1±31.0 °C(Predicted) | [density ]
1.155±0.06 g/cm3(Predicted) | [storage temp. ]
Store at 0°C | [form ]
powder to crystal | [pka]
15.97±0.20(Predicted) | [color ]
White to Almost white | [Optical Rotation]
Consistent with structure | [Major Application]
peptide synthesis | [InChI]
1S/C10H18N2O3/c1-10(2,3)15-9(14)12-6-4-5-7(12)8(11)13/h7H,4-6H2,1-3H3,(H2,11,13)/t7-/m0/s1 | [InChIKey]
PITJAAIPVBVRAO-ZETCQYMHSA-N | [SMILES]
CC(C)(C)OC(=O)N1CCC[C@H]1C(N)=O | [CAS DataBase Reference]
35150-07-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P264-P270-P301+P312a-P330-P501a | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
2
| [HS Code ]
2933.99.9701 | [REACH Registrations]
Active | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white powder | [Uses]
1-Boc-L-prolinamide is a reagent that is used in the preparation of thiazole amide peptidomimetics as erratum inhibitor apoptosis protein antagonist. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
GENERAL METHOD: BOC-L-proline (1.00 g, 4.65 mmol), di-tert-butyl dicarbonate (1.52 g, 6.97 mmol), ammonium bicarbonate (0.55 g, 6.97 mmol), and pyridine (1.0 mL) were dissolved in dioxane (20 mL), and the reaction was stirred at room temperature for 6 hours. After completion of the reaction, the product was extracted with dichloromethane, the organic phase was washed sequentially with 1 M hydrochloric acid and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. To the concentrate was added n-hexane (100 mL) and sonication prompted the product to precipitate as a white solid to afford N-tert-butoxycarbonyl-L-prolinamide (0.85 g, 85% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.37-4.34 (m, 1H), 3.47-3.36 (m, 2H), 2.07-1.85 (m, 4H), 1.49 (s, 9H). Mass spectrum (ESI) m/z 215 [M + H]+. | [References]
[1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 1719 - 1729
[2] Canadian Journal of Chemistry, 2007, vol. 85, # 2, p. 85 - 95
[3] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 35, p. 8544 - 8551
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 228 - 247
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 23, p. 7418 - 7429 |
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