Sodium Hydroxide → HCID 178434827, compound

HRID 632962Notes

Reaction equation

HRID 632962 reaction equation
C[O:2][C:3](=[O:38])[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:37])[CH2:19][CH2:20][NH:21][C:22]([C:24]3[N:25]=[C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])[O:27][C:28]=3[CH3:29])=[O:23])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+]>C1COCC1.O>[Cl:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:26]1[O:27][C:28]([CH3:29])=[C:24]([C:22]([NH:21][CH2:20][CH2:19][C:18]([NH:17][C:14]2[CH:13]=[CH:12][C:11]([C@H:8]3[CH2:9][CH2:10][C@H:5]([CH2:4][C:3]([OH:38])=[O:2])[CH2:6][CH2:7]3)=[CH:16][CH:15]=2)=[O:37])=[O:23])[N:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500673HCID 178500673, compound

Product 1

HCID 178434827HCID 178434827, compoundYield 98.6%

Reagents, catalysts & solvents 1

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

Procedure

Trans-{4-[4-(3-{[2-(2-chlorophenyl)-5-methyloxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester (80 mg, 0.149 mmol) was put into THF/water (20 mL, 3:1) solvent, and NaOH (44.61 mg, 1.115 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 a compound (77 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-01b27e983d634d3983dd3d561a5a25a6
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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