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

HRID 451867노트

반응식

HRID 451867 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7c10b6e8df794ab78bcc16b9d584b0d9
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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