n-Phenyloxycarbonyl-n-(2-allyloctanoyl)-1-(r)-phenylethylamine → Methyl 2-allyloctanoate

HRID 1180700Notes

Reaction equation

HRID 1180700 reaction equation
C1(OC(N([C@@H](C2C=CC=CC=2)C)[C:11](=[O:22])[CH:12]([CH2:19][CH:20]=[CH2:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=O)C=CC=CC=1.[O:31]([CH3:33])[Li]>CO>[CH2:19]([CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:11]([O:31][CH3:33])=[O:22])[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 69502119n-Phenyloxycarbonyl-n-(2-allyloctanoyl)-1-(r)-phenylethylamineHCID 178419045HCID 178419045, compound

Product 1

HCID 23117480Methyl 2-allyloctanoateYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.218 g (0.5 mmol) of N-phenyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine in 2 ml of methanol was cooled to 0° C., 0.38 g (1.0 mmol) of LiOMe was added, and the mixture was stirred for 22 hours. The reaction was terminated by addition of 2 ml of 1 N hydrochloric acid, and the product was extracted with ethyl acetate (30 ml×2). The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was quantitated by GC. Thus was obtained 0.057 g (58%) of the title compound.

Workup

  1. customThe reaction was terminated by addition of 2 ml of 1 N hydrochloric acid
  2. extractionthe product was extracted with ethyl acetate (30 ml×2)
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-a794d48e54f14c3ea733562610667c5b
Source dataset
uspto-grants-2007_10
Patent number
US07282605B2

Reaction notes

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