N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER synthesis
- 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
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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
501-53-1
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114676-59-4
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155075-23-3
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130930-25-5
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74-88-4
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155075-23-3
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501-53-1
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114676-47-0
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155075-23-3
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7732-18-5
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584-08-7
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501-53-1
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$10.00/1g
2584-71-6
341 suppliers
$6.00/1g
155075-23-3
77 suppliers
$29.00/250mg