Sodium Hydroxide → HCID 178525556, compound

HRID 632953Notes

Reaction equation

HRID 632953 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][CH:38]=[CH:37][C:36]=4[F:41])[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:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:28]1[O:29][C:30]([C:31]([F:34])([F:32])[F:33])=[C:26]([C:24]([NH:23][CH2:22][CH2:21][C:20]([NH:19][C:16]2[CH:15]=[CH:14][C:13]([C@H:10]3[CH2:9][CH2:8][C@H:7]([CH2:6][C:5]([OH:43])=[O:4])[CH2:12][CH2:11]3)=[CH:18][CH:17]=2)=[O:42])=[O:25])[N:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500675HCID 178500675, compound

Product 1

HCID 178525556HCID 178525556, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

NaOH (22.6 mg, 0.57 mmol) was added to trans-{4-[4-(3-{[2-(2-fluoro-phenyl)-5-trifluoromethyloxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester (65 mg, 0.11 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 of 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 (60 mg, 94%) 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-e5dd87dce9644df2911298eb5bdb1dc4
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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