Methanol → (S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate

HRID 451867ノート

反応式

HRID 451867 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C)C.CO>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][OH:11])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:3])([CH3:2])[CH3:4]

参加物

5

反応物 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 7018756(S)-2-((tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid

生成物 1

HCID 11107667(S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution (S)-2-(tert-butoxycarbonylamino)-5-methoxy-5-oxopentanoic acid (26.1 g, 0.1 mol) in THF (500 mL), BH3.Me2S (80 mL, 0.8 mmol) was added dropwise at −78° C., then stirred at rt for 3 hrs. The reaction was stopped by careful addition of methanol. After evaporation and three distillations of methanol, the residue was dissolved in EtOAc, washed with 1 M NaHCO3, and brine. (S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate (12 g, yield 49%) was obtained as an oil that was used in the next step without further purification.

後処理

  1. customAfter evaporation and three distillations of methanol
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with 1 M NaHCO3, and brine

出典と根拠

ORDレコード
ord-7c10b6e8df794ab78bcc16b9d584b0d9
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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