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

HRID 30526Notes

Reaction equation

HRID 30526 reaction equation
[C:1]([O:6][CH:7]([O:9][C:10]([NH:12][CH2:13][CH:14]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:15][C:16]([O:18]CC1C=CC=CC=1)=[O:17])=[O:11])[CH3:8])(=[O:5])[CH:2]([CH3:4])[CH3:3]>C(O)C.[Pd]>[C:1]([O:6][CH:7]([O:9][C:10]([NH:12][CH2:13][CH:14]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:15][C:16]([OH:18])=[O:17])=[O:11])[CH3:8])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

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

Product 1

HCID 160592343-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl]-5-Methylhexanoic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (41) (270 mg, 0.663 mmol) in ethanol (20 mL) was stirred with 10% Pd on carbon (11 mg) in a 50 mL round-bottomed flask under an atmosphere of hydrogen gas (balloon). The reaction was judged complete in 30 min. (monitoring by TLC and LC/MS). The mixture was filtered through a pad of Celite, and the solvent removed in vacuo to afford the title compound (33) as a mixture of two diastereomers (177 mg, 84%). 1H—NMR (CDCl3, 400 MHz): δ 0.89 (m, 6H), 1.16 (m, 8H), 1.46 (d, 3H), 1.66 (m, 1H), 2.11-2.36 (m, 3H), 2.52 (m, 1H), 3.11 (m, 1H), 3.27 (m, 1H), 5.08 (t, 1H), 6.77 (m, 1H). MS (ESI) m/z 316.20 (M−H−).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cf8414fce1e547b1875dcfcfe1f93824
Source dataset
uspto-grants-2008_09
Patent number
US07423169B2

Reaction notes

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