Vinyl hexanoate → (2R)-2-t-Butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanol

HRID 562635

반응식

HRID 562635 반응식
[C:1]([O:5][C:6]([NH:8][C:9]([CH2:14][CH3:15])([CH2:12][OH:13])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](OC=C)(=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C(OC(C)C)(C)C>[C:1]([O:5][C:6]([NH:8][C@@:9]([CH2:14][CH3:15])([CH2:10][O:11][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:12][OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 76451Vinyl hexanoateHCID 222796962-t-Butoxycarbonylamino-2-ethylpropane-1,3-diol

생성물 1

HCID 86596707(2R)-2-t-Butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanol수율 87.3%

시약·촉매·용매 1

HCID 7914Diisopropyl Ether용매

실험 절차

To a suspension of 2-t-butoxycarbonylamino-2-ethylpropane-1,3-diol (52.9 g, 241 mmol) in isopropyl ether (1.0 l) were added successively vinyl hexanoate (41 ml, 254 mmol) and lipase [Immobilized lipase from Pseudomonas sp., TOYOBO, 0.67 U/mg] (2.1 g) with stirring, and the resulting mixture was stirred at room temperature for 4 hours. After stirring, the reaction mixture was filtered and evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (7:1-4:1-2:1) as the eluent to afford the title compound (66.8 g, yield: 87%).

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 4 hours
  2. stirringAfter stirring
  3. filtrationthe reaction mixture was filtered
  4. customevaporated in vacuo
  5. customthe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-69eba05483de49edb4125ae2b9e68897
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067396B2

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