Methanol → HCID 57587974, compound

HRID 1782046Notes

Reaction equation

HRID 1782046 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][N:6]([C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.O.CO.O.[OH-].[Li+]>C1COCC1>[CH2:24]([O:23][C:21]([N:6]([CH2:5][C:4]([OH:27])=[O:3])[CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:22])[CH:25]=[CH2:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57587980HCID 57587980, compound

Product 1

HCID 57587974HCID 57587974, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(RS)-{Allyloxycarbonyl-[(4-chloro-phenyl)-phenyl-methyl]-amino}-acetic acid ethyl ester (18 g, 46.4 mmol) was dissolved in THF (60 mL), water (60 mL), and MeOH (60 mL) and treated with lithium hydroxide monohydrate (3.9 g, 92 mmol) at 20° C. for 2 h. The mixture was evaporated and extracted with AcOEt, 1 N HCl and 50% NaCl. The crude product was crystallized from heptane/ethyl acetate 10:1 (100 mL). One obtained 11.08 g (66%) of white crystals. MS: m/z=358 [M+H]+.

Workup

  1. customThe mixture was evaporated
  2. extractionextracted with AcOEt, 1 N HCl and 50% NaCl
  3. customThe crude product was crystallized from heptane/ethyl acetate 10:1 (100 mL)

Sources & evidence

ORD record
ord-d77408e7d6e04f77944eea3ea5207b47
Source dataset
uspto-grants-2009_03
Patent number
US07498339B2

Reaction notes

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