Hydrochloric Acid → HCID 69241635, compound

HRID 854668Notes

Reaction equation

HRID 854668 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:10][C:11]([CH3:30])=[C:12]([CH2:14][O:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][C@H:18]([CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])[CH2:17]3)[N:13]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Li+].Cl>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:10][C:11]([CH3:30])=[C:12]([CH2:14][O:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][C@H:18]([CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH2:17]3)[N:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69241617HCID 69241617, compound

Product 1

HCID 69241635HCID 69241635, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

110 mg of ethyl 4-{cis-3-[2-(3-methoxyphenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl}butyrate are dissolved in 5 ml of a mixture of tetrahydrofuran and water in a ratio of 2:1, and 20 mg of lithium hydroxide are added. The mixture is stirred at room temperature for 12 hours. The mixture is acidified by addition of 1 N HCl and extracted with ethyl acetate. The organic phase is dried over MgSO4, and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. Freeze-drying gives 24 mg of 4-{cis-3-[2-(3-methoxyphenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl}butyric acid as a lyophilizate. C22H29NO5 (387.48), MS(ESI): 388 (M+H+).

Workup

  1. additionare added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over MgSO4
  4. customthe solvent is then removed under reduced pressure
  5. customThe residue is purified by RP-HPLC
  6. customFreeze-drying

Sources & evidence

ORD record
ord-bf6279a8456649dbb8b198bb69c1ac37
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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