Chemical Products N-benzyloxycarbonyl-d-proline Production Methods

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CAS No:6404-31-5
Formula:C13H15NO4
Synonyms:D-Z-PRO;Z-D-PRO-OH;Z-D-PROLINE;CBZ-D-PRO-OH;CBZ-D-PROLINE;N-Z-D-PROLINE;Z-D-PYRD(2)-OH;N-CBZ-D-PRO-OH;N-CBZ-D-PROLINE;(+)-Z-D-proline
China Export:From 2018.11 to 2019.11, total export volume of N-Benzyloxycarbonyl-D-proline from China was 112,377,052KG while total export value was $2,146,929,254. The biggest proportion of exporting volume in the last 12 months was 9.88% in 2019.03.

Chemical Products N-Benzyloxycarbonyl-D-proline Description
White crystalline powder or powder

Chemical Products N-Benzyloxycarbonyl-D-proline Basic Attributes
CAS No：6404-31-5

Molecular Formula ：C13H15NO4

Molecular Mass ：249.26

Exact Mass ：249.100113

PSA ：66.8 A^2

LogP ：1.7

EINECS ：229-021-5

InChIKeys ：JXGVXCZADZNAMJ-LLVKDONJSA-N

H-bond Acceptor ：4

H-bond Donor ：1

SP3 ：0.38

RBN ：4

Chemical Products N-Benzyloxycarbonyl-D-proline Characteristics
Appearance ：White Crystalline Powder or Powder

Density ：1.3±0.1 ...
... g/cm3

Melting Point ：76-78 °C(lit.)

Bolling Point ：432.3°C at 760 mmHg

Flash Point ：215.3±28.7 °C

Refractive Index ：1.582

Storage Condition ：Store at RT.

BRN ：485188

Specific Rotation ：40 º (c=2, EtOH)

Chemical Products N-Benzyloxycarbonyl-D-proline Safety Information
HS Code ：29339900

UN No. ：NONH for all modes of transport

WGK_Germany ：3

Safety Instructions ：24/25

Dangerous Mark ：Xi

P Code ：P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements ：H315

Chemical Products N-Benzyloxycarbonyl-D-proline Production Methods
Step-1 : Preparation of (R)-l-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (12a) To a stirred solution of D-Proline (1.2 g, 10.42 mmol) in 2 N aqueous NaOH solution (20.85 mL, 41.7 mmol) at 0 °C was added benzyl chloroformate (1.488 mL, 10.42 mmol) and allowed to warm to room temperature overnight. The reaction was washed with MTBE (2 x 25 mL), acidified with cone HCl and extracted with ethyl acetate (2 x 200 mL). The ethyl acetate layers were combined washed with water (50 mL), brine (25 mL) dried and concentrated in vacuum to afford (R)-l-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (12a) (2.41 g, 9.67 mmol, 93 percent yield) which was used as such in next step; Η NMR (300 MHz, DMSO-i) δ 12.66 (s, 1H), 7.42 - 7.25 (m, 5H), 5.14 - 4.97 (m, 2H), 4.20 (ddd, J = 22.7, 8.8, 3.5 Hz, 1H), 3.50 - 3.25 (m, 2H), 2.32 - 2.08 (m, 1H), 1.97 - 1.75 (m, 3H); MS (ES+) 250.2 (M+l), 272.2 (M+Na), (ES-) 248.2 (M-l), 284.2 (M+Cl), 497.4 (2M-1).20.0mmol D-valine was dissolved in 12.0mL, 2mol/L NaOH solution, 22mmol benzyl chloroformate was added dropwise at 0 °C, then added with NaOH solution, extracted, washed, dried, concentrated, separated by silica gel column. Got(R)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylic acid in a yield of 95percent.