tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate → (1,1-dimethyl ethyl) N-(5-bromo-7-fluoro-2-benzoxazolyl)-O-(4-ethoxy-4-oxo-butyl)-L-tyrosinate

HRID 1759712ノート

反応式

HRID 1759712 の反応式
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][C@@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH2:15])=[CH:11][CH:10]=1)[CH3:2].[Br:26][C:27]1[CH:28]=[C:29]([F:38])[C:30]2[O:34][C:33](SC)=[N:32][C:31]=2[CH:37]=1>C([O-])(=O)C.C([O-])(=O)C.[Hg+2]>[Br:26][C:27]1[CH:28]=[C:29]([F:38])[C:30]2[O:34][C:33]([NH:15][C@H:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:13][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:25])=[CH:24][CH:23]=3)=[N:32][C:31]=2[CH:37]=1

参加物

4

反応物 2

HCID 15512208tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionateHCID 225994905-Bromo-7-fluoro-2-(methylthio)-benzoxazole

生成物 1

HCID 69880648(1,1-dimethyl ethyl) N-(5-bromo-7-fluoro-2-benzoxazolyl)-O-(4-ethoxy-4-oxo-butyl)-L-tyrosinate収率 40.5%

試薬・触媒・溶媒 1

HCID 15337Mercuric acetate触媒

反応条件

温度
100 °C

実験手順

The mixture constituted by aminoester 4-2 (865 mg; 2.46 mmoles), 5-bromo-7-fluoro-2-(methylthio)-benzoxazole (804 mg; 3.07 mmoles) and mercury diacetate (437 mg) is agitated for 3 hours, under nitrogen and at 100° C. After cooling down, the medium is chromatographed eluting with a CH2Cl2/ethyl acetate mixture 95/5, 564 mg of expected product is obtained, which is repurified by recrystallizing from isopropyl oxide. 528 mg of purified product is obtained.

後処理

  1. temperatureAfter cooling down
  2. customthe medium is chromatographed
  3. washeluting with a CH2Cl2/ethyl acetate mixture 95/5

出典と根拠

ORDレコード
ord-57cb84ae0b3540efbaee501e8b58cb22
出典データセット
uspto-grants-2005_01
特許番号
US06838453B2

反応ノート

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