| Identification | More | [Name]
N-Benzyloxycarbonyl-L-proline | [CAS]
1148-11-4 | [Synonyms]
1,2-PYRROLIDINEDICARBOXYLIC ACID, 1-(PHENYLMETHYL) ESTER, (2S)-
1-[(BENZYLOXY)CARBONYL]-L-PROLINE
(2S)-1-[(BENZYLOXY)CARBONYL]PYRROLIDINE-2-CARBOXYLIC ACID
BENZYLOXYCARBONYL-L-PROLINE
CARBOBENZYLOXY-L-PROLINE
CBZ-L-PROLINE
CBZ-PRO-OH
L-CBZ-PROLINE
N-ALPHA-BENZYLOXYCARBONYL-L-PROLINE
N-ALPHA-CARBOBENZOXY-L-PROLINE
N-ALPHA-CARBOBENZOXY-L-PYRROLIDINE-2-CARBOXYLIC ACID
N-ALPHA-CBZ-L-PROLINE
N-BENZYLOXYCARBONYL-L-PROLINE
N-CARBOBENZOXY-L-PROLINE
N-CARBOBENZYLOXY-L-PROLINE
N-CBZ-L-PROLINE
N-CBZ-L-PROLINE-OH
(S)-N-CBZ-PYRROLIDINE-2-CARBOXYLIC ACID
Z-L-PRO-OH
Z-PROLINE | [EINECS(EC#)]
214-557-4 | [Molecular Formula]
C13H15NO4 | [MDL Number]
MFCD00003170 | [Molecular Weight]
249.26 | [MOL File]
1148-11-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
75-77 °C | [alpha ]
-60 º (c=2,AcOH) | [Boiling point ]
392.36°C (rough estimate) | [density ]
1.1952 (rough estimate) | [refractive index ]
-40 ° (C=2, EtOH) | [storage temp. ]
2-8°C
| [solubility ]
Solubility in methanol, almost transparency. | [form ]
Crystalline Powder or Crystals | [pka]
3.99±0.20(Predicted) | [color ]
White to off-white | [optical activity]
[α]20/D 42°, c = 2 in ethanol | [BRN ]
88579 | [InChIKey]
JXGVXCZADZNAMJ-NSHDSACASA-N | [CAS DataBase Reference]
1148-11-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R62:Possible risk of impaired fertility.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
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
| [RTECS ]
UY0745000
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
N-(Benzyloxycarbonyl)-L-proline is a potent in vitro and in vivo inhibitor of prolidase; a specific peptidase that cleaves dipeptides with a C-terminal prolyl and hydroxylprolyl residue. It is also used in the synthesis of N-(L-Prolyl)-β-alanine which is a derivative of the naturally occurring beta amino acid β-Alanine. | [Preparation]
Caution! All procedures must be carried out in an efficient fume cupboard, wearing latex gloves and chemical-proof safety goggles. ι-Proline (10.0 g, 8.7 mmol) was dissolved in 2 m sodium hydroxide solution (40 mL), and the solution was cooled to ice-water temperature. Z-Cl (20.5 g, 12 mmol) was added portionwise, with vigorous stirring or occasional shaking, over a period of 30 min at 0–5 °C to the solution of l-proline. The ice bath was then removed and stirring or occasional shaking was continued for 30 min while the reaction mixture warmed to room temperature. The mixture was then acidified to Congo red by the gradual addition of concentrated hydrochloric acid, and the oil was extracted into ethyl acetate. The extract was dried over magnesium sulfate, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was extracted/triturated with warm tetrachloromethane. The washings were decanted and the residue was further purified by recrystallization from ethyl acetate/petroleum ether. |
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