5-(4-(Trifluoromethyl)phenyl)pentan-1-ol → (R)-tert-Butyl 2,2,4-trimethyl-4-(2-oxo-2-(3-(trifluoromethyl)-4-(5-(4-(trifluoromethyl)phenyl)pentyloxy)phenyl)ethylcarbamoyl)oxazolidine-3-carboxylate

HRID 2357084Notes

Reaction equation

HRID 2357084 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:28])[CH2:9][NH:10][C:11]([C@@:13]2([CH3:27])[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[N:14]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:12])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].[F:33][C:34]([F:48])([F:47])[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]O)=[CH:37][CH:36]=1>C(#N)C.O>[CH3:18][C:15]1([CH3:19])[N:14]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C@@:13]([CH3:27])([C:11](=[O:12])[NH:10][CH2:9][C:8](=[O:28])[C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][C:38]3[CH:37]=[CH:36][C:35]([C:34]([F:33])([F:47])[F:48])=[CH:40][CH:39]=3)=[C:3]([C:29]([F:31])([F:32])[F:30])[CH:4]=2)[CH2:17][O:16]1

Participants

4

Reactant 2

HCID 593843295-(4-(Trifluoromethyl)phenyl)pentan-1-olHCID 59384415(R)-tert-Butyl 4-(2-(4-hydroxy-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)-2,2,4-trimethyloxazolidine-3-carboxylate

Product 1

HCID 59384448(R)-tert-Butyl 2,2,4-trimethyl-4-(2-oxo-2-(3-(trifluoromethyl)-4-(5-(4-(trifluoromethyl)phenyl)pentyloxy)phenyl)ethylcarbamoyl)oxazolidine-3-carboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared from (R)-tert-butyl 4-(2-(4-hydroxy-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)-2,2,4-trimethyloxazolidine-3-carboxylate (0.25 mmol, 1.0 equiv) and 5-(4-(trifluoromethyl)phenyl)pentan-1-ol (0.25 mmol, 1.0 equiv) according to the general procedure in 31% yield. HPLC retention time on a C18 column (30×4.6 mm, 3.5 V) was 3.26 min with gradient 50-95% acetonitrile-H2O (0.1% TFA) in 3.5 min as mobile phase. MS (ESI, M+H+)=675.6.

Sources & evidence

ORD record
ord-91838d150607447095fd87cae2f961fb
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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