Isobutyric Acid → Methyl 1-{[(alpha-Isobutanoyloxyisobutoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

HRID 457290Notes

Reaction equation

HRID 457290 reaction equation
Cl[CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])[CH:3]([CH3:5])[CH3:4].[C:22]([OH:27])(=[O:26])[CH:23]([CH3:25])[CH3:24]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[C:22]([O:27][CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])[CH:3]([CH3:5])[CH3:4])(=[O:26])[CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 6590Isobutyric Acid2×HCID 66584224Methyl 1-{[(alpha-Chloroisobutoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

Product 1

HCID 66584350Methyl 1-{[(alpha-Isobutanoyloxyisobutoxy)carbonyl]aminomethyl}-1-Cyclohexane AcetateYield 63.3%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

A mixture of (106) (760 mg, 2.38 mmol), silver carbonate (394 mg, 1.4 mmol), and isobutyric acid (442 μL, 4.76 mmol) in chloroform was stirred at room temperature for 24 h. Another batch of silver carbonate (394 mg, 1.4 mmol) and isobutyric acid (442 μL, 4.76 mmol) was added, and the resulting mixture was stirred for another 24 h. After filtration, the filtrate was concentrated and the resulting residue purified by silica gel flash column chromatography, eluting with 10% ethyl acetate/hexane, to afford 560 mg (63%) of the title compound. 1H NMR (CDCl3, 400 MHz): δ 0.94 (d, J=6.8 Hz, 3H), 0.96 (d, J=6.8 Hz, 3H), 1.15 (d, J=7.2 Hz, 3H), 1.17 (d, J=7.2 Hz, 3H), 1.32–1.58 (m, 10H), 2.01 (m, 1H), 2.19 (s, 2H), 2.55 (m, 1H), 3.18 (m, 2H), 3.67 (s, 3H), 5.33 (t, 1H), 6.56 (d, J=4.8 Hz, 1H). MS (ESI) m/z 372.38 (M+H+).

Workup

  1. stirringthe resulting mixture was stirred for another 24 h
  2. filtrationAfter filtration
  3. concentrationthe filtrate was concentrated
  4. customthe resulting residue purified by silica gel flash column chromatography
  5. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0be467d0bdcb43d497da1f1af607906c
Source dataset
uspto-grants-2007_03
Patent number
US07186855B2

Reaction notes

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