Hydrochloric Acid → HCID 131724077, compound

HRID 1168439Notes

Reaction equation

HRID 1168439 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][O:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]([CH3:34])=[C:27]([CH:33]=4)[C:28]([O:30]CC)=[O:29])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.[OH-].[K+].Cl>CC(C)(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][O:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]([CH3:34])=[C:27]([CH:33]=4)[C:28]([OH:30])=[O:29])[CH2:16]3)[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 131724078HCID 131724078, compound

Product 1

HCID 131724077HCID 131724077, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 47 mg of ethyl rac-cis-5-{3-[2-(4-fluorophenyl)oxazol-4-ylmethoxy]cyclohexyloxymethyl}-2-methylbenzoate 24, 2 ml of 1,1-dimethylethanol and 50% (w/w) potassium hydroxide was heated at 85° C. (oil bath) for 2 hours. The pH was adjusted to 3 using dilute hydrochloric acid and the mixture was extracted twice with MTBE. The extracts were dried over magnesium sulfate, filtered and concentrated on a rotary evaporator, and the product was then purified by chromatography. This gave the product 20 of molecular weight 439.49 (C25H26FNO5); MS (ESI): 440 (M+H+).

Workup

  1. extractionthe mixture was extracted twice with MTBE
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated on a rotary evaporator
  5. customthe product was then purified by chromatography

Sources & evidence

ORD record
ord-f2e9d475d0e74aba90bf3e7c61d23a0e
Source dataset
uspto-grants-2003_09
Patent number
US06624185B2

Reaction notes

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