Hydrogen Bromide → 6-chloro-L-tryptophan

HRID 616262ノート

反応式

HRID 616262 の反応式
C([O:3][C:4]([C:6]1(C(OCC)=O)[CH2:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[NH2:18])=[CH:8][N:7]1C(=O)C)=[O:5])C.Br>>[Cl:17][C:14]1[CH:13]=[C:12]2[C:11](=[CH:16][CH:15]=1)[C:9]([CH2:10][C@@H:6]([C:4]([OH:3])=[O:5])[NH2:7])=[CH:8][NH:18]2

参加物

3

反応物 2

HCID 260Hydrogen BromideHCID 128785021-Acetyl-4-(2-amino-4-chlorophenyl)-2,3-dihydro-1H-pyrrole-2,2-dicarboxylic acid diethylester

生成物 1

HCID 100626936-chloro-L-tryptophan収率 91.1%

実験手順

A mixture of 60 g (0.16 mol) of the compound of Example 11, and 450 ml. of 2 N aqueous HBr was heated under N2 at 95° for 30 hours. The solution was concentrated in vacuo and the residual salt was taken up in 300 ml of water. The solution was brought to pH 5.5 with 4N NaOH and the mixture was chilled in an icebath for 1 hour. The precipitate was collected, washed with cold water and dried to give 34.8 g of product. Crystallization from glacial acetic acid (360 ml.) afforded, after drying at 100°/0.2 mmHg, 30.8 g (82%) of white crystals, m.p. 280° (dec.) (lit. m.p. 285°-286°), which was identical with an authentic sample.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. temperaturethe mixture was chilled in an icebath for 1 hour
  3. customThe precipitate was collected
  4. washwashed with cold water
  5. customdried

出典と根拠

ORDレコード
ord-3d12bec7184442f3959b844d35772bd4
出典データセット
uspto-grants-1978_02
特許番号
US04073795

反応ノート

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