Hydrochloric Acid → HCID 59751032, compound

HRID 748035Notes

Reaction equation

HRID 748035 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([O:19][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:32]=[CH:31][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:29][CH:28]=4)[O:24][C:25]=3[CH3:26])[CH2:14]2)[C:3]=1[C:4]([O-:6])=[O:5].Cl>C(O)(C)(C)C.[OH-].[K+]>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([O:19][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:28]=[CH:29][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:31][CH:32]=4)[O:24][C:25]=3[CH3:26])[CH2:14]2)[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86760718HCID 86760718, compound

Product 1

HCID 59751032HCID 59751032, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

90 mg of Methyl [2-methyl-6-[(1R,3S)-3-(5-methyl-2-(4-(2-propyl)-phenyl)-oxazol-4-ylmethoxy)-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. The reaction is monitored by TLC. 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 69 mg of 2-methyl-6-[(1R,3S)-3-(5-methyl-2-(4-(2-propyl)-phenyl)-oxazole-4-ylmethoxy)-cyclohexyloxymethyl]-benzoic acid as an amorphous solid. C29H35NO5 (477.61), MS(ESI): 478 (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-4bc49b9d307a4cdf858eecb6c7d88f06
Source dataset
uspto-grants-2008_07
Patent number
US07399777B2

Reaction notes

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