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Ethanol → benzyl ((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-1-isopropylbutyl)carbamate

HRID 906957
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HRID 906957 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:28]([CH3:30])[CH3:29])[CH:13]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:14][C:15](OCC)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].C(O)C>C1COCC1.C(OCC)(=O)C>[Si:21]([O:20][CH:13]([CH2:14][CH2:15][OH:16])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:28]([CH3:30])[CH3:29])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 67390315ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-{[tert-butyl(dimethyl)silyl]oxy}-5-methylhexanoate

생성물 1

HCID 86640708benzyl ((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-1-isopropylbutyl)carbamate수율 93.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

실험 절차

Under an argon atmosphere, to a suspension (303 mL) of ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-{[tert-butyl(dimethyl)silyl]oxy}-5-methylhexanoate (17.7 g), calcium chloride (6.73 g) and sodium borohydride (4.58 g) in dehydrated THF was added with stirring under ice-cooling dehydrated ethanol (152 mL), and the mixture was gradually warmed to room temperature and stirred for 15 hr. The reaction mixture was slowly poured into a mixture of ethyl acetate and ice water (containing 1 mol/L hydrochloric acid, 122 mL) and the mixture was partitioned. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=19/1→1/1) to give benzyl ((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-1-isopropylbutyl)carbamate as colorless oil (yield: 14.9 g).

후처리

  1. stirringstirred for 15 hr
  2. customthe mixture was partitioned
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=19/1→1/1)

출처 및 근거

ORD 기록
ord-2c36faa00f764cba848ee15c192bd6ec
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08013008B2

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