ChemicalBook CAS DataBase List N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER

N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER synthesis

11synthesis methods

Product Name:N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER
CAS Number:155075-23-3
Molecular formula:C14H17NO5
Molecular Weight:279.29

2584-71-6 Synthesis

2584-71-6
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$6.00/1g

N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER

155075-23-3
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$29.00/250mg

Yield: 100%

Reaction Conditions:

with sodium hydrogencarbonate in water;toluene at 23; for 24.25 h;

Steps:

92.1 Preparation of 1-(3,4-dimethoxy-5-trifluoromethylthiobenzoyl)-4R-methoxypyrrolidine- 2R-carboxylic acid hydroxyamide; Step 1
To a stirred solution of 4R-hydroxypyrrolidine-2R-carboxylic acid (5.02 g, 38.3 mmol, 1 eq. ) and [NAHC03] (8.05 g, 95.8 mmol, 2.5 eq. ) in H20 (85 mL) at 23 [°C] was added a solution of Cbz-Cl (6.28 mL, 44.0 mmol, 1.15 eq. ) in toluene (20 mL) over 15 min period. After 24 h the layers were separated and the aqueous layer was extracted with Et2O (2 x 100 mL) and discarded the combined organic layer. The aqueous layer was then acidified to pH 2 with concentrated [HCI,] and the product was extracted with EtOAc (2 x 100 mL). The organic layer was dried and concentrated in vacuo to give [4R-HYDROXYPYRROLIDINE-1,] [2R-DICARBOXYLIC] acid [1-] benzyl ester 2-methyl ester (9.97 g, [100%)

References:

VICURON PHARMACEUTICALS, INC. WO2004/7444, 2004, A2 Location in patent:Page 139