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

HRID 748010Notes

Reaction equation

HRID 748010 reaction equation
F[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:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:24]=4[C:25]([OH:27])=[O:26])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.[C:33](OCC)(=[O:35])C.Cl>C[O-].[Na+].CO>[CH3:33][O:35][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:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:24]=4[C:25]([OH:27])=[O:26])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 59094663(+)-cis-2-(3-(2-(4-Fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic Acid2×

Product 1

HCID 69796958cis-2-(3-(2-(4-Methoxyphenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic Acid

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

170 mg (0.39 mmol) of 6b were heated in 4 ml of 5.6 M NaOMe/MeOH solution at an oil bath temperature of 120° C. for 20 hours. Ethyl acetate and 2 N HCl were added, and the mixture was then worked up analogously to the synthesis of 6b. This gave 7b as a colorless amorphous solid. TLC: (methylene chloride/methanol/conc. ammonia, 30/5/1). Rf˜0.3. C26H29NO6 (451.52) MS(ESI): 452 (M+H+).

Sources & evidence

ORD record
ord-5d56a53571f94550bb379b842accdd8b
Source dataset
uspto-grants-2008_07
Patent number
US07399777B2

Reaction notes

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