Sodium Hydroxide → HCID 178501063, compound

HRID 1893344Notes

Reaction equation

HRID 1893344 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](=[O:16])[NH:12][CH2:13][CH:14]=O)[CH2:7][CH2:6]1)=[O:4].P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[O:16][CH:14]=[CH:13][N:12]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178501161HCID 178501161, compound

Product 1

HCID 178501063HCID 178501063, compoundYield 23%

Conditions

Temperature
100 °C

Procedure

A mixture of trans-4-(2-oxo-ethylcarbamoyl)-cyclohexanecarboxylic acid methyl ester (830 mg, 3.65 mmol) and phosphorus oxychloride (2.80 g, 18.3 mmol) was heated at 100° C. for 20 h. After cooling to room temperature the reaction mixture was poured on crushed ice and basified to pH 7-8 by addition of 1 M aqueous sodium hydroxide solution. The mixture was extracted with three 100 ml-portions of ethyl acetate. The combined organic layers were washed with one 50 ml-portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification with n-heptane/ethyl acetate as eluent gave the title compound (175 mg, 23%) as white solid, with a purity of 90% according to GC. MS m/e: 210 ([M+H]+)

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. additionwas poured
  3. customon crushed ice
  4. extractionThe mixture was extracted with three 100 ml-portions of ethyl acetate
  5. washThe combined organic layers were washed with one 50 ml-portion of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification with n-heptane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-42492ef5d11940b0b5ccc85d1c46b840
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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