Sodium Hydroxide → HCID 178525558, compound

HRID 632955Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

NaOH (23.94 mg, 0.56 mmol) was added to trans-{4-[4-(3-{[2-(2,4-dichlorophenyl)-5-trifluoromethyloxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester (75 mg, 0.12 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. Then, the filtrate was eluted with a gradient of methanol/DCM (5-10%) on a silica gel by column chromatography and purified. Accordingly, the desired compound (71 mg, 97%) was obtained as a white solid.

Workup

concentrationconcentrated under vacuum
stirringstirred for 30 minutes
filtrationfiltered
washThen, the filtrate was eluted with a gradient of methanol/DCM (5-10%) on a silica gel by column chromatography
custompurified

Sources & evidence

ORD record: ord-2c5c9929d87b4b9e86c647437a729c37
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321728B2

Reaction notes

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