Water → HCID 117818750, compound

HRID 2206879Notes

Reaction equation

HRID 2206879 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=1[CH:16]1[O:20][N:19]=[C:18]([C:21](=O)[CH2:22]Cl)[CH2:17]1)(=[O:4])=[O:3].[C:25]([CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1)(=[S:27])[NH2:26].O>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:13])[F:14])[CH:9]=[CH:8][C:7]=1[CH:16]1[O:20][N:19]=[C:18]([C:21]2[N:26]=[C:25]([CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)[S:27][CH:22]=2)[CH2:17]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 962WaterHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 117818895HCID 117818895, compound

Product 1

HCID 117818750HCID 117818750, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-(chloroacetyl)-4,5-dihydro-1,2-oxazol-5-yl]-5-(trifluoromethyl)phenyl methanesulphonate (200 mg) and tert-butyl 4-carbamothioylpiperidine-1-carboxylate (108 mg) in tetrahydrofuran (2 ml) at room temperature was added tetrabutylammonium bromide. The reaction mixture was stirred at room temperature for 12 hours. Then water was added thereto, and the aqueous phase was removed and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. Purification by column chromatography gave tert-butyl 4-[4-(5-{2-[(methylsulphonyl)oxy]-4-(trifluoromethyl)phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (168 mg, 56%).

Workup

  1. customthe aqueous phase was removed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-49f2e7ef2612413994a1f8ced08e28e4
Source dataset
uspto-grants-2016_06
Patent number
US09375009B2

Reaction notes

Loading…