Lithium Hydroxide → (R)-2-(4-Phenoxymethyl-benzyloxycarbonylamino)-3-phenyl-propionic Acid

HRID 1827963Notes

Reaction equation

HRID 1827963 reaction equation
C[O:2][C:3](=[O:31])[C@H: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][CH:28]=[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-]>CO.O>[O:24]([CH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][O:15][C:13]([NH:12][C@H:4]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([OH:31])=[O:2])=[O:14])=[CH:18][CH:19]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 12990904(R)-2-(4-Phenoxymethyl-benzyloxycarbonylamino)-3-phenyl-propionic Acid Methyl Ester

Product 1

HCID 11463863(R)-2-(4-Phenoxymethyl-benzyloxycarbonylamino)-3-phenyl-propionic AcidYield 77.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

(R)-2-(4-Phenoxymethyl-benzyloxycarbonylamino)-3-phenyl-propionic acid methyl ester 6 (1.605 g, 3.83 mmol) was dissolved in methanol (40ml) at room temperature. A solution of LiOH (177 mgs, 4.21 mmol) in 15ml of H2O was then added and the mixture was stirred overnight. The mixture was diluted with H2O (50 ml). The methanol was then removed in vacuo. The aqueous residue was acidified with 4.5N HCl forming a precipitate that was filtered and dried. Recrystallization gave about 1.2 g of (R)-2-(4-phenoxymethyl-benzyloxycarbonylamino)-3-phenyl-propionic acid 7, mp. 115.9–116.70C.

Workup

  1. customThe methanol was then removed in vacuo
  2. filtrationwas filtered
  3. customdried
  4. customRecrystallization

Sources & evidence

ORD record
ord-76906e6382ec4626ae60500ede4eaaee
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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