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

HRID 1633274노트

반응식

HRID 1633274 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9bd3fbb4db004d4b9b55a4e9cdbe2aee
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04479942

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