Hydrochloric Acid → HCID 12990922, compound

HRID 1827983Notes

Reaction equation

HRID 1827983 reaction equation
C[O:2][C:3](=[O:32])[CH:4]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Li+].[OH-].Cl>CO.O>[F:31][C:28]1[CH:27]=[CH:26][C:25]([O:24][CH2:23][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][O:15][C:13]([NH:12][CH:4]([CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:3]([OH:32])=[O:2])=[O:14])=[CH:22][CH:21]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 12990921HCID 12990921, compound

Product 1

HCID 12990922HCID 12990922, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

2-[4-(4-Fluoro-phenoxymethyl)benzyloxycarbonyl]amino-3-phenyl-propionic acid methyl ester 38 (115 mg) was dissolved in 10 ml methanol, then treated with 1.1 equiv LiOH in water. After 2 hrs at 60° C., the mixture was poured into water, acidified with HCl, and extracted The organic phase was dried, evaporated and recrystallized to yield about 74 mg of 2-[4-(4-fluorophenoxymethyl) benzyloxycarbonyl]amino-3-phenyl-propionic acid 40, mp. 111.8–113.4° C.

Workup

  1. extractionextracted The organic phase
  2. customwas dried
  3. customevaporated
  4. customrecrystallized

Sources & evidence

ORD record
ord-58e9a3ad3f844cec823b5b9fc0d12f50
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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