Phenol → (S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl)ethanone

HRID 710046Notes

Reaction equation

CN(C=O)C.CS([O:10][CH2:11][C:12]1[O:13][C:14]([C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:37])[C:23]([F:36])([F:35])[C:24]2([OH:34])[CH2:29][C:28]([CH3:31])([CH3:30])[CH2:27][C:26]([CH3:33])([CH3:32])[CH2:25]2)=[N:15][N:16]=1)(=O)=O.[C:38]1(O)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C([O-])([O-])=O.[K+].[K+]>O>[F:35][C:23]([F:36])([C:24]1([OH:34])[CH2:29][C:28]([CH3:31])([CH3:30])[CH2:27][C:26]([CH3:33])([CH3:32])[CH2:25]1)[C:22]([N:18]1[CH2:19][CH2:20][CH2:21][C@H:17]1[C:14]1[O:13][C:12]([CH2:11][O:10][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[N:16][N:15]=1)=[O:37]

Participants

Conditions

Temperature: 50 °C

Procedure

To a DMF (1.0 mL) solution of the compound (32.5 mg) obtained in Example 9-(6) and phenol (13 mg), K2CO3 (37 mg) was added and the mixture was stirred at 50° C. for 3.5 hours. The reaction mixture was added to water (20 mL) and the organic layer extracted with AcOEt (20 mL×2) was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (31.6 mg, colorless amorphous.)

Workup

extractionthe organic layer extracted with AcOEt (20 mL×2)
dry with materialwas dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give a crude product, which
customwas further purified by silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record: ord-2a6c891141924db0aa5504d315b12518
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181229B2

Reaction notes

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