Methyl chloroacetate → N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosine

HRID 1633274Notes

Reaction equation

HRID 1633274 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:22][C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

Product 1

HCID 59910020N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosineYield 135.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of diphenylmethyl ester of N-tert-butoxycarbonyl-L-tyrosine (5.00 g), methyl chloroacetate (1.45 g) and potassium carbonate (1.85 g) in N,N-dimethylformamide (75 ml) was stirred for 20 hours at room temperature. The mixture was diluted with water (100 ml) and extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid, aqueous sodium bicarbonate, and then brine. After dried over magnesium sulfate, the extract was evaporated to dryness to give diphenylmethyl ester of N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosine (6.40 g), mp. 69°-73° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with diluted hydrochloric acid, aqueous sodium bicarbonate
  3. dry with materialAfter dried over magnesium sulfate
  4. customthe extract was evaporated to dryness

Sources & evidence

ORD record
ord-9bd3fbb4db004d4b9b55a4e9cdbe2aee
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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