Trifluoroacetic acid → dibenzyl ((2S,3S,5S)-3-hydroxy-1,6-diphenylhexane-2,5-diyl)dicarbamate

HRID 443106ノート

反応式

HRID 443106 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C@H:20]1[O:41][C@@H:21]1[C@@H:22]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].FC(F)(F)C(O)=O>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C@@H:20]([OH:41])[CH2:21][C@@H:22]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 15384541(2S,3R,4R,5S)-2,5-bis-(N-(((benzyl)oxy)carbonyl)amino)-3,4-epoxy-1,6-diphenylhexane

生成物 1

HCID 460972dibenzyl ((2S,3S,5S)-3-hydroxy-1,6-diphenylhexane-2,5-diyl)dicarbamate収率 58.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 39.2 g (71.2 mmol) of (2S,3R,4R,5S)-2,5-bis-(N-(((benzyl)oxy)carbonyl)amino)-3,4-epoxy-1,6-diphenylhexane in 600 ml of THF was treated under N2 atmosphere with 13 g (0.36 mol) of sodium borohydride. The resulting mixture was treated dropwise with 27.7 ml (0.36 mol) of trifluoroacetic acid. After being stirred for 3.5 h at ambient temperature, the resulting mixture was quenched with 1N aqueous HCl, diluted with water, and stirred for 16 h. The resulting mixture was filtered. washed with water, and dried to provide 22.85 g (58%) of the desired compound as a white solid.

後処理

  1. customthe resulting mixture was quenched with 1N aqueous HCl
  2. additiondiluted with water
  3. stirringstirred for 16 h
  4. filtrationThe resulting mixture was filtered
  5. washwashed with water
  6. customdried

出典と根拠

ORDレコード
ord-16ec08877fec46c9874ca30ec39e61b2
出典データセット
uspto-grants-1999_04
特許番号
US05892052

反応ノート

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