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

HRID 1633274ノート

反応式

HRID 1633274 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 59910020N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosine収率 135.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9bd3fbb4db004d4b9b55a4e9cdbe2aee
出典データセット
uspto-grants-1984_10
特許番号
US04479942

反応ノート

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