Sodium Hydroxide → HCID 178525559, compound

HRID 632951Notes

Reaction equation

HRID 632951 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:43])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:42])[CH2:21][CH2:22][NH:23][C:24]([C:26]3[N:27]=[C:28]([C:35]4[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=4)[O:29][C:30]=3[C:31]([F:34])([F:33])[F:32])=[O:25])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1>C1COCC1.CO.O>[F:41][C:38]1[CH:39]=[CH:40][C:35]([C:28]2[O:29][C:30]([C:31]([F:33])([F:32])[F:34])=[C:26]([C:24]([NH:23][CH2:22][CH2:21][C:20]([NH:19][C:16]3[CH:17]=[CH:18][C:13]([C@H:10]4[CH2:9][CH2:8][C@H:7]([CH2:6][C:5]([OH:43])=[O:4])[CH2:12][CH2:11]4)=[CH:14][CH:15]=3)=[O:42])=[O:25])[N:27]=2)=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500679HCID 178500679, compound

Product 1

HCID 178525559HCID 178525559, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

NaOH (30.9 mg, 0.8 mmol) was added to trans-{4-[4-(3-{[2-(4-fluorophenyl)-5-trifluoromethyloxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester solution (89 mg, 0.16 mmol) dissolved in THF/MeOH/water (20 mL, 3:2:1). The reaction mixture was stirred at 25° C. for 15 hours and concentrated under vacuum. The residue was acidified with 1M HCl up to pH 2, stirred for 30 minutes, and filtered. The filtrate was eluted with a gradient of methanol/DCM (5-10%) on a silica gel by column chromatography and purified to obtain the desired compound (75 mg, 86%) as a white solid.

Workup

  1. concentrationconcentrated under vacuum
  2. stirringstirred for 30 minutes
  3. filtrationfiltered
  4. washThe filtrate was eluted with a gradient of methanol/DCM (5-10%) on a silica gel by column chromatography
  5. custompurified

Sources & evidence

ORD record
ord-bf9cffaebc454f87a49ebd2744f0353d
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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