benzyl trifluoroacetyl-L-serinate → benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinate

HRID 2165233ノート

反応式

HRID 2165233 の反応式
[C:1]([O:4][C@H:5]([CH3:21])[C@@H:6]([C:18]([OH:20])=[O:19])[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])(=[O:3])[CH3:2].[F:22][C:23]([F:41])([F:40])[C:24]([NH:26][C@H:27]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:28]O)=[O:25]>C(Cl)Cl>[C:1]([O:4][C@H:5]([CH3:21])[C@H:6]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:18]([O:20][CH2:28][C@@H:27]([C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])[NH:26][C:24](=[O:25])[C:23]([F:22])([F:40])[F:41])=[O:19])(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 14357546benzyl trifluoroacetyl-L-serinateHCID 18640002O-acetyl-N-benzyloxycarbonyl-L-threonine

生成物 1

HCID 18639967benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinate収率 73.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of O-acetyl-N-benzyloxycarbonyl-L-threonine (1 g) and benzyl N-trifluoroacetyl-L-serinate (987 mg) in methylene chloride (20 ml) was added N,N-diethylaminopropyl-N'-ethylcarbodiimide hydrochloride (1.22 g) and 4-N,N-dimethylaminopyridine (77.8 mg) at room temperature. After stirring for an hour at room temperature, the reaction mixture was washed successively with aqueous hydrogen chloride, water, 10% aqueous sodium hydrogen carbonate and brine. After drying over sodium sulfate, the methylene chloride extract was filtered and concentrated. The residue was chromatographed on silica gel (20 g) eluting successively with a mixture of hexane and methylene chloride (1:1), methylene chloride and a mixture of methylene chloride and acetone (125:1) to give benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxo-butyl]-N-trifluoroacetyl-L-serinate (1.42 g).

後処理

  1. washthe reaction mixture was washed successively with aqueous hydrogen chloride, water, 10% aqueous sodium hydrogen carbonate and brine
  2. dry with materialAfter drying over sodium sulfate
  3. extractionthe methylene chloride extract
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (20 g)
  7. washeluting successively with a mixture of hexane and methylene chloride (1:1), methylene chloride
  8. additiona mixture of methylene chloride and acetone (125:1)

出典と根拠

ORDレコード
ord-1059afd4609c49ac9334cb5a4acaa2ca
出典データセット
uspto-grants-1990_07
特許番号
US04939241

反応ノート

読み込み中…