| Identification | More | [Name]
Z-PRO-NH2 | [CAS]
34079-31-7 | [Synonyms]
2-CARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER
BENZYLOXYCARBONYL-L-PROLINAMIDE
CARBOBENZYLOXY-L-PROLINAMIDE
CBZ-L-PROLINAMIDE
CBZ-L-PRO NH2
CBZ-PRO-NH2
N-ALPHA-CARBOBENZOXY-L-PROLINE AMIDE
N-ALPHA-CARBOBENZOXY-L-PYRROLIDINE-2-CARBOXYLIC ACID ALPHA-AMIDE
N-CARBOBENZOXY-L-PROLINE AMIDE
(S)-1-N-CBZ-PROLINAMIDE
(S)-2-CARBAMOYL-1-CBZ-PYRROLIDINE
(S)-2-CARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER
Z-L-PROLINAMIDE
Z-L-PROLINE AMIDE
Z-PROLINE-NH2
Z-PRO-NH2
Z-PYRD(2)-NH2
N-BENZYLOXYCARBONYL-L-PROLINAMIDE
N-alpha-Benzyloxycarbonyl-L-proline amide
Z-L-Pro-NH2 | [EINECS(EC#)]
231-397-0 | [Molecular Formula]
C13H16N2O3 | [MDL Number]
MFCD00020830 | [Molecular Weight]
248.28 | [MOL File]
34079-31-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
90-95℃ | [Boiling point ]
465.6±44.0 °C(Predicted) | [density ]
1.263±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT. | [solubility ]
soluble in Methanol | [form ]
Solid | [pka]
15.95±0.20(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C13H16N2O3/c14-12(16)11-7-4-8-15(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H2,14,16)/t11-/m0/s1 | [InChIKey]
ZCGHEBMEQXMRQL-NSHDSACASA-N | [SMILES]
N1(C(OCC2=CC=CC=C2)=O)CCC[C@H]1C(N)=O | [CAS DataBase Reference]
34079-31-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White crystals | [Uses]
peptide synthesis | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
General procedure for the synthesis of (S)-1-N-benzyloxycarbonylproline from N-benzyloxycarbonyl-L-proline: 1-{[(phenylmethyl)oxy]carbonyl}-L-proline (8.0 g, 32.09 mmol) was solubilized in 1,4-dioxane (40 mL), and pyridine (1.5 mL) and di-tert-butyl dicarbonate ((Boc)2O, 9.1 g 41.72 mmol). Ammonium bicarbonate (3.2 g, 40.43 mmol) was then added. The reaction mixture was stirred at room temperature overnight and then diluted with ethyl acetate (100 mL) and washed sequentially with water (50 mL) and 5% sulfuric acid (H2SO4). The organic layer was separated, dried over anhydrous sodium sulfate (Na2SO4) and filtered. The solvent was removed by distillation under reduced pressure to give a clarified oil. The oily material was ground with ether, the precipitate was collected by filtration and dried under vacuum to afford (S)-1-N-Benzyloxycarbonylprolinamide as a white solid (3.9 g, 49% yield). The mass spectrum showed [M+H]+ of 249. | [References]
[1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 1, p. 84 - 96
[2] Synlett, 2004, # 3, p. 558 - 560
[3] Patent: WO2005/121135, 2005, A1. Location in patent: Page/Page column 240-241
[4] Canadian Journal of Chemistry, 2007, vol. 85, # 2, p. 85 - 95
[5] Journal of the American Chemical Society, 2018, vol. 140, # 5, p. 1627 - 1631 |
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