Isobutyric Acid → Benzyl 3-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-5-Methyl-Hexanoate

HRID 30525

반응식

HRID 30525 반응식
Cl[CH:2]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:6])[CH3:3].CN1CCOCC1.[C:32]([OH:37])(=[O:36])[CH:33]([CH3:35])[CH3:34]>ClCCl>[C:32]([O:37][CH:2]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:6])[CH3:3])(=[O:36])[CH:33]([CH3:35])[CH3:34]

참가 물질

5

반응물 3

HCID 6590Isobutyric Acid2회HCID 79724-MethylmorpholineHCID 21113521Benzyl 3-{[(alpha-Chloroethoxy)carbonyl]aminomethyl}-5-Methyl-Hexanoate

생성물 1

HCID 66887904Benzyl 3-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-5-Methyl-Hexanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (40) (0.53 g, 1.50 mmol) in isobutyric acid (1 mL) was added to a mixture of isobutyric acid (0.96 mL, 10.8 mmol) and N-methylmorpholine (1.14 mL, 10.4 mmol) at room temperature. The resulting reaction mixture was stirred at room temperature for 48 h. The reaction mixture was diluted with dichloromethane, washed successively with water, 10% aqueous NaHCO3 solution and brine, then dried over anhydrous Na2SO4. After filtration and removal of the solvent in vacuo, the residue was purified by flash chromatography on silica gel, eluting with 5% ethyl acetate in hexane to afford the title compound (41) as a mixture of two diastereomers (400 mg, 66%). 1H—NMR (CDCl3, 400 MHz): δ 0.85 (m, 6H), 1.14 (m, 8H), 1.44 (m, 3H), 1.62 (m, 1H), 2.13 (m, 1H), 2.32 (m, 2H), 2.51 (m, 1H), 3.06 (m, 1H), 3.24 (m, 1H) 4.95 (m, 1H), 5.10 (s, 2H), 6.76 (q, 1H).

후처리

  1. customThe resulting reaction mixture
  2. washwashed successively with water, 10% aqueous NaHCO3 solution and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration and removal of the solvent in vacuo
  5. customthe residue was purified by flash chromatography on silica gel
  6. washeluting with 5% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-7215531b15434df8beee00b176cccbb1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423169B2

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