Sodium Hydroxide → HCID 178525552, compound

HRID 632964Notes

Reaction equation

HRID 632964 reaction equation
C[O:2][C:3](=[O:37])[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:36])[CH2:19][CH2:20][NH:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)=[O:23])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+]>C1COCC1.O>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][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:37])=[O:2])[CH2:10][CH2:9]3)=[CH:12][CH:13]=2)=[O:36])=[O:23])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500669HCID 178500669, compound

Product 1

HCID 178525552HCID 178525552, compoundYield 96.3%

Reagents, catalysts & solvents 1

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

Procedure

Trans-[4-(4-{3-[(biphenyl-4-carbonyl)amino]propionylamino}phenyl)cyclohexyl]acetic acid methyl ester (60 mg, 0.120 mmol) was put into THF/water (20 mL, 3:1) solvent, and NaOH (38.51 mg, 0.963 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 (56 mg, 96%) 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-48ca810e318f4d17943a788affbed118
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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