Dimethyl Sulfoxide → HCID 57888675, compound

HRID 1016149Notes

Reaction equation

Cl[CH2:2][C:3]([NH:5][C@H:6]([CH:25]([CH3:27])[CH3:26])[C:7]([N:9]1[CH2:14][CH2:13][C@@:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([OH:15])[C:11]([CH3:24])([CH3:23])[CH2:10]1)=[O:8])=[O:4].C(=O)([O-])[O-].[K+].[K+].[OH:34][C:35]1[CH:44]=[CH:43][CH:42]=[CH:41][C:36]=1[C:37]([O:39][CH3:40])=[O:38].CS(C)=O>CCOC(C)=O>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C@@:12]2([OH:15])[CH2:13][CH2:14][N:9]([C:7](=[O:8])[C@H:6]([NH:5][C:3](=[O:4])[CH2:2][O:34][C:35]3[CH:44]=[CH:43][CH:42]=[CH:41][C:36]=3[C:37]([O:39][CH3:40])=[O:38])[CH:25]([CH3:27])[CH3:26])[CH2:10][C:11]2([CH3:23])[CH3:24])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

2-Chloro-N-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)acetamide (35 mg, 0.084 mmol), potassium carbonate (35 mg, 0.253 mmol), methyl 2-hydroxybenzoate (13 mg, 0.084 mmol) and DMSO (3 mL) were mixed with stirring at 25° C. The reaction was stirred for 20 hours, diluted with EtOAc, and then rinsed 4 times with water. The organic layer was dried over sodium sulfate and concentrated in vacuo to give an amber oil which was purified over silica gel in (3:1 to 1:1 hexanes/EtOAc to 100% EtOAc) to obtain methyl 2-(2-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-2-oxoethoxy)benzoate (18 mg, 0.034 mmol, 40% yield) as a white glass. MS found: (M+H)+=531.21.

Workup

stirringThe reaction was stirred for 20 hours
washrinsed 4 times with water
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customto give an amber oil which
customwas purified over silica gel in (3:1 to 1:1 hexanes/EtOAc to 100% EtOAc)

Sources & evidence

ORD record: ord-5f219314c7514fa5accf5b06ee279915
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985861B2

Reaction notes

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