Hydrochloric Acid → (+)-cis-2-(3-(2-(4-Fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic Acid

HRID 748009Notes

Reaction equation

HRID 748009 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:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:24]=4[C:25]([O:27]C)=[O:26])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.[OH-].[K+].Cl>CC(O)(C)C.C(OCC)(=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:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:24]=4[C:25]([OH:27])=[O:26])[CH2:16]3)[N:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58681954Methyl cis-2-(3-(2-(4-fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoate

Product 1

HCID 59094663(+)-cis-2-(3-(2-(4-Fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic Acid

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.2 g (9.2 mmol) of 5b were dissolved in 120 ml of t-BuOH. 50 ml of 50% aq. KOH were added, and the mixture was then boiled at 100° C. for 24 hours. For work-up, the mixture was allowed to cool and then diluted with 100 ml of ethyl acetate. The aqueous phase was made slightly acidic by addition of 2 N aqueous HCl and extracted 2 more times with 100 ml of ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated, and the residue was purified by flash chromatography (methylene chloride/methanol/conc. ammonia, 30/5/1). This gave 6b as a white amorphous solid. TLC (methylene chloride/methanol/conc. ammonia, 30/5/1). Rf=0.3. Recrystallization from toluene. C25H26FNO5 (432.42) MS(ESI): 433 (M+H+).

Workup

  1. temperatureto cool
  2. extractionextracted 2 more times with 100 ml of ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography (methylene chloride/methanol/conc. ammonia, 30/5/1)

Sources & evidence

ORD record
ord-56be79db4fb1466c894fd7bc09aacd2c
Source dataset
uspto-grants-2008_07
Patent number
US07399777B2

Reaction notes

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