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

HRID 970785Notes

Reaction equation

HRID 970785 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 (40 ml) at room temperature. A solution of LiOH (177 mgs, 4.21 mmol) in 15 ml 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. 115.9-116.7° C.

Workup

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

Sources & evidence

ORD record
ord-a2cb171dc23543b08510ed995115ddc2
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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