Sodium Hydroxide → HCID 59659278, compound

HRID 253361Notes

Reaction equation

HRID 253361 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([O:22][CH2:23][C:24]2([C:27]([O:29]CC)=[O:28])[CH2:26][CH2:25]2)[CH2:17]1.[OH-].[Na+]>CO>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([O:22][CH2:23][C:24]2([C:27]([OH:29])=[O:28])[CH2:26][CH2:25]2)[CH2:17]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59659237HCID 59659237, compound

Product 1

HCID 59659278HCID 59659278, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

56 mg of ethyl (1R,3S)-1-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]cyclopropanecarboxylate are dissolved in 3 ml of methanol, 0.5 ml of 5N NaOH is added and the mixture is stirred at room temperature for 18 h. The solvent is removed under reduced pressure and the residue is acidified with trifluoroacetic acid and purified by RP-HPLC. This gives (1R,3S)-1-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]cyclopropanecarboxylic acid as a colorless oil. C23H29NO5 (399.49), MS (ESI): 400 (M+H+).

Workup

  1. customThe solvent is removed under reduced pressure
  2. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-7564c0d4c9ef4f8289de420afb19371d
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Reaction notes

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