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

HRID 1168438Notes

Reaction equation

HRID 1168438 reaction equation
[C:1](OCC)(=[O:3])C.Cl.F[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]=[C:18]([CH2:20][O:21][C@@H:22]3[CH2:27][CH2:26][CH2:25][C@H:24]([O:28][CH2:29][C:30]4[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[C:31]=4[C:32]([OH:34])=[O:33])[CH2:23]3)[N:19]=2)=[CH:11][CH:10]=1>C[O-].[Na+].CO>[CH3:1][O:3][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]=[C:18]([CH2:20][O:21][C@@H:22]3[CH2:27][CH2:26][CH2:25][C@H:24]([O:28][CH2:29][C:30]4[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[C:31]=4[C:32]([OH:34])=[O:33])[CH2:23]3)[N:19]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

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

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)of6b 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-32e352b6696948b49a534aebf0c0971e
Source dataset
uspto-grants-2003_09
Patent number
US06624185B2

Reaction notes

Loading…