Trifluoroacetic acid → (2S,3S)-2-(2-amino-3-phenyl-butyrylamino)-thiazole-4-carboxylic acid methyl ester

HRID 32828

反応式

HRID 32828 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:29])[C@@H:12]([NH:21]C(OC(C)(C)C)=O)[C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[S:8][CH:9]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:29])[C@@H:12]([NH2:21])[C@H:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:14])[S:8][CH:9]=1)=[O:4]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 866033892-((2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyrylamino)-thiazole-4-carboxylic acid methyl ester

生成物 1

HCID 86603390(2S,3S)-2-(2-amino-3-phenyl-butyrylamino)-thiazole-4-carboxylic acid methyl ester収率 71.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-((2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyrylamino)-thiazole-4-carboxylic acid methyl ester (0.65 g, 1.54 mmol) was mixed in dichloromethane (5 mL) in an ice-bath. Trifluoroacetic acid (5 mL) was added and the solution was stirred for 2 hours. The reaction mixture was evaporated and the residue was precipitated with ether. The mixture was stirred vigorously for 10 minutes and then filtered. The solid was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with brine and dried (sodium sulfate). Evaporation of the solvents gave 2-((2S,3S)-2-amino-3-phenyl-butyrylamino)-thiazole-4-carboxylic acid methyl ester (0.35 g, 71%).

後処理

  1. customThe reaction mixture was evaporated
  2. customthe residue was precipitated with ether
  3. stirringThe mixture was stirred vigorously for 10 minutes
  4. filtrationfiltered
  5. customThe solid was partitioned between aqueous sodium bicarbonate and dichloromethane
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with dichloromethane
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried (sodium sulfate)
  10. customEvaporation of the solvents

出典と根拠

ORDレコード
ord-0d892e3e44a74ef9849795f2cc5c39e5
出典データセット
uspto-grants-2008_09
特許番号
US07427635B2

関連ノート

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