Sodium Hydroxide → HCID 178525560, compound

HRID 632959Notes

Reaction equation

HRID 632959 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:41])[CH2:19][CH2:20][NH:21][C:22]([C:24]3[N:25]=[C:26]([C:33]4[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=4[Cl:40])[O:27][C:28]=3[C:29]([F:32])([F:31])[F:30])=[O:23])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+]>C1COCC1.O>[Cl:39][C:38]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:40])[C:33]=1[C:26]1[O:27][C:28]([C:29]([F:32])([F:30])[F:31])=[C:24]([C:22]([NH:21][CH2:20][CH2:19][C:18]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([C@H:8]3[CH2:7][CH2:6][C@H:5]([CH2:4][C:3]([OH:42])=[O:2])[CH2:10][CH2:9]3)=[CH:12][CH:13]=2)=[O:41])=[O:23])[N:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500680HCID 178500680, compound

Product 1

HCID 178525560HCID 178525560, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Trans-{4-[4-(3-{[2-(2,6-dichloro-phenyl)-5-trifluoromethyloxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester (459 mg, 0.733 mmol) was put into THF/water (50 mL, 3:1) solvent, and NaOH (146.54 mg, 3.663 mmol) was added thereto. The mixture was stirred for 24 hours, THF was removed, and pH of the mixture was adjusted to be 2-3 with 1N hydrochloric acid. The reaction mixture was extracted with EtOAC (3×100 mL), washed with brine and dried with anhydrous sodium sulfate, and the solvent was removed. The obtained crude material was crystallized with acetonitrile to obtain the desired compound (434 mg, 97%) as a white solid.

Workup

  1. additionwas added
  2. customTHF was removed
  3. extractionThe reaction mixture was extracted with EtOAC (3×100 mL)
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customThe obtained crude material
  8. customwas crystallized with acetonitrile

Sources & evidence

ORD record
ord-01e7c56e14ef4749a2fe8e84457ed663
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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