Sodium Hydroxide → HCID 178525554, compound

HRID 632957Notes

Reaction equation

HRID 632957 reaction equation
C[O:2][C:3](=[O:44])[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:43])[CH2:19][CH2:20][NH:21][C:22]([C:24]3[N:25]=[C:26]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]([F:42])([F:41])[F: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>[F:32][C:29]([F:30])([F:31])[C:28]1[O:27][C:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]([F:42])([F:41])[F:40])=[N:25][C:24]=1[C:22]([NH:21][CH2:20][CH2:19][C:18]([NH:17][C:14]1[CH:13]=[CH:12][C:11]([C@H:8]2[CH2:9][CH2:10][C@H:5]([CH2:4][C:3]([OH:44])=[O:2])[CH2:6][CH2:7]2)=[CH:16][CH:15]=1)=[O:43])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500672HCID 178500672, compound

Product 1

HCID 178525554HCID 178525554, compoundYield 98%

Reagents, catalysts & solvents 1

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

Procedure

Trans-{4-[4-(3-{[5-trifluoromethyl-2-(2-trifluoromethylphenyl)oxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester (455 mg, 0.727 mmol) was put into THF/water (50 mL, 3:1) solvent, and NaOH (145.47 mg, 3.637 mmol) was added thereto. The mixture was stirred at room temperature 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 (435 mg, 98%) 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-490fb3c26b9b4a73b7ba1c6f429a9971
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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