Sodium Hydroxide → (1R,3S)-2-Methyl-6-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethoxy}benzoic acid

HRID 553571

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Unpurified ethyl (1R,3S)-2-methyl-6-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethoxy}benzoate are dissolved in 3 ml of methanol, and 0.25 ml of a 5 N sodium hydroxide solution are added. The mixture is stirred at 60° C. for 8 h and at 80° C. for 12 h. After cooling, the mixture is taken up in 2N HCl/ethyl acetate, the organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by RP-HPLC. This gives (1R,3S)-2-methyl-6-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethoxy)benzoic acid as a colorless oil. C28H33NO6 (479.58), MS (ESI). 480 (M+H+).

Workup

temperatureAfter cooling
dry with materialthe organic phase is dried over sodium sulfate
customthe solvent is removed under reduced pressure
customThe residue is purified by RP-HPLC

Sources & evidence

ORD record: ord-be0d8dec52454863864b00770e568257
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048901B2

Linked notes

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