Benzyl Alcohol → (S)-Benzyl 3-(benzoylaminomethyl)-5-methylhexanoate

HRID 48538Notes

Reaction equation

HRID 48538 reaction equation
[CH2:1](O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([NH:17][CH2:18][C@@H:19]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:20][C:21]([OH:23])=[O:22])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[C:9]([NH:17][CH2:18][C@@H:19]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:20][C:21]([O:23][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:22])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 9813903(S)-3-(Benzoylaminomethyl)-5-methylhexanoic acid

Product 1

HCID 15551905(S)-Benzyl 3-(benzoylaminomethyl)-5-methylhexanoateYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzyl alcohol (0.31 g, 3.0 mmol) was added to a stirred mixture of (S)-3-(benzoylaminomethyl)-5-methylhexanoic acid 4 (0.78 g, 3.0 mmol), 1,3-dicyclo-hexylcarbodiimide (0.61 g, 3.0 mmol), and 4-dimethylaminopyridine (0.36 g, 3.0 mmol) in dichloromethane (40 ml) and the mixture was stirred for 18 hours. The reaction mixture was, filtered and concentrated in vacuo. The residue was chromatographed (SiO2, heptane-ether, 1:0 to 75:25) to give 5(0.83 g, 79%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed (SiO2, heptane-ether, 1:0 to 75:25)

Sources & evidence

ORD record
ord-27e65473b07b4a7d82522535a19e5e3f
Source dataset
uspto-grants-2004_03
Patent number
US06703522B2

Reaction notes

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