Hydrochloric Acid → 2-{3-[2-(4-Bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic Acid

HRID 748014Notes

Reaction equation

HRID 748014 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:34])=[C:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH: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.Cl>C(O)(C)(C)C.[OH-].[K+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH3:34])=[C:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH: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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22493646Methyl 2-{3-[2-(4-bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoate

Product 1

HCID 224936372-{3-[2-(4-Bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic Acid

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

117 mg of 49 were stirred in a mixture of 10 ml of tert-butanol and 1 ml of 10 N aqueous potassium hydroxide solution at 90° C. After two days, the mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, the solvents were removed under reduced pressure and the residue was purified by RP-HPLC. This gave 50 as an amorphous solid. C26H28BrNO5 (514.52), MS(ESI): 514.29, 516.29 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customthe solvents were removed under reduced pressure
  4. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-99620e5a1faa4ae0841fba473a50f3ac
Source dataset
uspto-grants-2008_07
Patent number
US07399777B2

Reaction notes

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