Lithium Hydroxide → N-(3-methyl-2(S)-(t-butoxycarbonylamino)but-1-yl)phenylalanine

HRID 1900630Notes

Reaction equation

HRID 1900630 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:28])[C@H:6]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:7][CH2:8][C@@H:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:10]([CH3:12])[CH3:11]>O.COCCOC>[CH3:11][CH:10]([CH3:12])[C@H:9]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:8][NH:7][C@H:6]([C:5]([OH:28])=[O:4])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22846564N-(3-methyl-2(S)-(t-butoxycarbonylamino)-but-1-yl)phenylalanine methyl ester

Product 1

HCID 22846563N-(3-methyl-2(S)-(t-butoxycarbonylamino)but-1-yl)phenylalanineYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of lithium hydroxide (1.63 g, 0.068 mole) in water (70 ml) was added to a solution of the product of Step A (7.6 g, 0.021 mole) in ethylene glycol dimethyl ether (100 ml) with cooling in an ice bath. The reaction mixture was stirred at room temperature under Ar for 2 hours, concentrated in vacuo, and extracted (2×) with ethyl acetate. The aqueous phase was neutralized with 10% of citric acid, cooled and filtered to give the product as a white solid (6.6 g), mp >193° (dec).

Workup

  1. temperaturewith cooling in an ice bath
  2. concentrationconcentrated in vacuo
  3. extractionextracted (2×) with ethyl acetate
  4. temperaturecooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bb31e7f4a05a48b2872052cdb28cff2b
Source dataset
uspto-grants-1996_11
Patent number
US05576293

Reaction notes

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