Acetic Acid → HCID 59295421, compound

HRID 2233290Notes

Reaction equation

HRID 2233290 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2(Br)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:8][C:7]=1[CH2:18]Br)=[O:5])[CH3:2].[H-].[Na+].[C:22](O)(=[O:24])[CH3:23]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:8][C:7]=1[CH2:18][O:24][CH2:22][CH3:23])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 59295387HCID 59295387, compound

Product 1

HCID 59295421HCID 59295421, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

1.25 g 2-(1-Bromo-cyclohexyl)-4-bromomethyl-oxazole-5-carboxylic acid ethyl ester was dissolved in 15 ml ethanol. 176 mg sodium hydride were added and the reaction mixture stirred at 65° C. for one hour. The cooled reaction mixture was neutralized by the addition of acetic acid (pH˜6). 50 mg palladium on charcoal (10%) were added and the reaction mixture was stirred under an atmosphere of hydrogen for one hour. The catalyst was filtered off through a pad of celite, the filtrate was evaporated in vacuo and the resulting crude material was purified by reversed phase HPLC to obtain 370 mg 2-Cyclohexyl-4-ethoxymethyl-oxazole-5-carboxylic acid ethyl ester as an oil.

Workup

  1. customThe cooled reaction mixture
  2. stirringthe reaction mixture was stirred under an atmosphere of hydrogen for one hour
  3. filtrationThe catalyst was filtered off through a pad of celite
  4. customthe filtrate was evaporated in vacuo
  5. customthe resulting crude material was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-a7aed501f98c43fcb7ca00d6d0d264d7
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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