Ammonium Chloride → tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-hydroxybutyl)cyclopropanecarboxylate

HRID 1173611노트

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HRID 1173611 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:25][CH3:26])[C:13]([C:15]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:25][CH3:26])[CH:13]([C:15]1([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:17][CH2:16]1)[OH:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 59556905tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}butanoyl)cyclopropanecarboxylate

생성물 1

HCID 67104998tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-hydroxybutyl)cyclopropanecarboxylate수율 78.4%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

To a solution of tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}butanoyl)cyclopropanecarboxylate (1.16 g) in methanol (25 mL) was added sodium borohydride (180 mg) at 0° C., and the mixture was stirred at 0° C. for 30 min. Aqueous ammonium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1) to give tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-hydroxybutyl)cyclopropanecarboxylate as a colorless oil (yield: 914.8 mg, yield: 78%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1)

출처 및 근거

ORD 기록
ord-525d4496337843718dd19910e8a1de32
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

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