Lithium Hydroxide → HCID 25121475, compound

HRID 1691950Notes

Reaction equation

HRID 1691950 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:49])[N:17]([CH3:48])[CH:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([C:33]3[N:34]=[C:35]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[O:36][C:37]=3[C:38]([F:41])([F:40])[F:39])=[O:32])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)=[O:10])C1C=CC=CC=1.[OH-].[Li+]>CO.O>[CH3:48][N:17]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([C:33]3[N:34]=[C:35]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[O:36][C:37]=3[C:38]([F:39])([F:40])[F:41])=[O:32])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)[C:16]([C@@H:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:49]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66738302HCID 66738302, compound

Product 1

HCID 25121475HCID 25121475, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Trans-2-[methyl-(1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidin-4-yl)-carbamoyl]-cyclopentanecarboxylic acid benzyl ester was hydrolyzed with lithium hydroxide in methanol and water. The resulted crude mixture was concentrated and the residue was dissolved in ethyl acetate and water with citric acid as acidifying agent. The organic layer then was concentrated and purified by reverse phase HPLC. The mixture of isomers was obtained as a yellow solid. LCMS calcd for C30H31F3N4O5 (m/e) 584, obsd 585 (M+H).

Workup

  1. customThe resulted crude mixture
  2. concentrationwas concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. concentrationThe organic layer then was concentrated
  5. custompurified by reverse phase HPLC
  6. additionThe mixture of isomers
  7. customwas obtained as a yellow solid

Sources & evidence

ORD record
ord-a7cfd3d3d95c4d13a28dee4b0ddc50cd
Source dataset
uspto-grants-2012_04
Patent number
US08153644B2

Reaction notes

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