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

HRID 30525

Reaction equation

HRID 30525 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7215531b15434df8beee00b176cccbb1
Source dataset
uspto-grants-2008_09
Patent number
US07423169B2

Linked notes

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