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

HRID 1269407

반응식

HRID 1269407 반응식
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH2:12][OH:13])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15](OC=C)(=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(OC(C)C)(C)C>[C:1]([O:5][C:6]([NH:8][C@@:9]([CH3:14])([CH2:10][O:11][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 76451Vinyl hexanoateHCID 11593669tert-butyl N-(1,3-dihydroxy-2-methylpropan-2-yl)carbamate

생성물 1

HCID 11630856(2R)-2-t-Butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol수율 85%

시약·촉매·용매 1

HCID 7914Diisopropyl Ether용매

실험 절차

To a suspension of 2-t-butoxycarbonylamino-2-methylpropane-1,3-diol (20.0 g, 97.4 mmol) in isopropyl ether (200 ml) were added successively vinyl hexanoate (16.3 ml, 0.10 mol) and lipase [Immobilized lipase from Pseudomonas sp., TOYOBO, 0.67 U/mg] (0.8 g) with stirring, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, the reaction mixture was filtered and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (10:1–2:1) as the eluent to afford the title compound (25.0 g, yield: 85%).

후처리

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

출처 및 근거

ORD 기록
ord-debf5abbbd5d4aac8586f5917ef1b786
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199150B2

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