2-Oxobutanoic Acid → HCID 15595770, compound

HRID 1638515Notes

Reaction equation

HRID 1638515 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.O=[C:12]([CH2:16][CH3:17])[C:13]([OH:15])=[O:14]>>[CH:1]1([CH2:6][CH2:7][C:8]([NH:10]/[C:12](=[CH:16]\[CH3:17])/[C:13]([OH:15])=[O:14])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 582-Oxobutanoic AcidHCID 918359HCID 918359, compound

Product 1

HCID 15595770HCID 15595770, compound

Procedure

A solution of 1.41 g (10 mmole) of 3-cyclopentylpropionamide and 1.53 g (15 mmole) of 2-ketobutyric acid was stirred and refluxed under a small Dean-Stark trap. After 8 hrs. the solution was cooled, resulting in heavy crystallization. The solid was collected on a filter and washed with toluene and CH2Cl2. Yield of white crystals=1.44 g, mp 180.5°-182° (prelim. softening). The material was recrystallized from methyl ethyl ketone. Yield of white needles=0.63 g (28%), mp 184°-185° (slight prelim. softening). Tlc (4:1 toluene-AcOH) now showed a single spot, and NMR indicated essentially pure Z-isomer.

Workup

  1. temperaturerefluxed under a small Dean-Stark trap
  2. temperaturethe solution was cooled
  3. customresulting in heavy crystallization
  4. customThe solid was collected on
  5. filtrationa filter
  6. washwashed with toluene and CH2Cl2
  7. customThe material was recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-ec701a497daf497fbe5afe52232c839b
Source dataset
uspto-grants-1989_11
Patent number
US04880793

Reaction notes

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