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

HRID 30525

反応式

HRID 30525 の反応式
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]

参加物

5

反応物 3

HCID 6590Isobutyric Acid2 回HCID 79724-MethylmorpholineHCID 21113521Benzyl 3-{[(alpha-Chloroethoxy)carbonyl]aminomethyl}-5-Methyl-Hexanoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7215531b15434df8beee00b176cccbb1
出典データセット
uspto-grants-2008_09
特許番号
US07423169B2

関連ノート

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