Hydrochloric Acid → 2-Methyl-6-[(1R,3S)3-(5-methyl-2-naphthalen-2-yloxazol-4-ylmethoxy)cyclo-hexyloxymethyl]benzoic Acid

HRID 1373163Notes

Reaction equation

HRID 1373163 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH:29]=4)[O:25][C:26]=3[CH3:27])[CH2:15]2)[C:3]=1[C:4]([O:6]C)=[O:5].Cl>C(O)(C)(C)C.[OH-].[K+]>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH:29]=4)[O:25][C:26]=3[CH3:27])[CH2:15]2)[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58781014HCID 58781014, compound

Product 1

HCID 121573952-Methyl-6-[(1R,3S)3-(5-methyl-2-naphthalen-2-yloxazol-4-ylmethoxy)cyclo-hexyloxymethyl]benzoic Acid

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

94 mg of methyl 2-methyl-6-[(1R,3S)3-(5-methyl-2-naphthalen-2-yloxazol-4-yl-methoxy]cyclohexyloxymethyl]benzoate are stirred at 90° C. in a mixture of 10 ml of tert-butanol and 1 ml of 10 N potassium hydroxide solution. After two days, the mixture is acidified with hydrochloric acid and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate, the solvents are removed under reduced pressure and the residue is purified by RP-HPLC. This gives 72 mg of 2-methyl-6-[(1R,3S)3-(5-methyl-2-naphthalen-2-yloxazol-4-yl-methoxy)cyclohexyloxymethyl]benzoic acid as an amorphous solid. C30H31NO5 (485.59), MS(ESI): 486 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-86477b17fa254068956a90b79a35b285
Source dataset
uspto-grants-2007_01
Patent number
US07160911B2

Reaction notes

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