Acetic Acid → 1-[(Pyrimidine-5-carbonyl)-amino]cyclopropanecarboxylic acid

HRID 1406328Notes

Reaction equation

HRID 1406328 reaction equation
[OH-].[Na+].[N:3]1[CH:8]=[C:7]([C:9]([NH:11][C:12]2([C:15]([O:17]CC)=[O:16])[CH2:14][CH2:13]2)=[O:10])[CH:6]=[N:5][CH:4]=1.C(O)(=O)C>CO>[N:3]1[CH:8]=[C:7]([C:9]([NH:11][C:12]2([C:15]([OH:17])=[O:16])[CH2:13][CH2:14]2)=[O:10])[CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67444517Ethyl 1-[(pyrimidin-5-ylcarbonyl)amino]-cyclopropanecarboxylate

Product 1

HCID 594962911-[(Pyrimidine-5-carbonyl)-amino]cyclopropanecarboxylic acidYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

65 mL of a 2N sodium hydroxide solution were added to a solution of 11.0 g (46.76 mmol) of ethyl 1-[(pyrimidine-5-carbonyl)amino]-cyclopropanecarboxylate in 200 mL methanol and the mixture was stirred for one hour at 50° C. Then it was neutralised with concentrated acetic acid and evaporated to dryness in vacuo. The crude product thus obtained was purified by chromatography.

Workup

  1. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-20e387da0bb8422ab62e989a5d71fe21
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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