Water → 2-{4-[4-(5-{2-[(Methylsulphonyl)oxy]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}-2-oxoethyl acetate

HRID 2206876Notes

Reaction equation

HRID 2206876 reaction equation
[Cl-].[CH3:2][S:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[O:17][N:16]=[C:15]([C:18]2[N:19]=[C:20]([CH:23]3[CH2:28][CH2:27][NH2+:26][CH2:25][CH2:24]3)[S:21][CH:22]=2)[CH2:14]1)(=[O:5])=[O:4].[C:29]([O:32][CH2:33][C:34](Cl)=[O:35])(=[O:31])[CH3:30].C(N(CC)CC)C.O>ClCCl>[C:29]([O:32][CH2:33][C:34]([N:26]1[CH2:27][CH2:28][CH:23]([C:20]2[S:21][CH:22]=[C:18]([C:15]3[CH2:14][CH:13]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[O:6][S:3]([CH3:2])(=[O:4])=[O:5])[O:17][N:16]=3)[N:19]=2)[CH2:24][CH2:25]1)=[O:35])(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 1178190674-[4-(5-{2-[(Methylsulphonyl)oxy]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidinium chloride

Product 1

HCID 1178188842-{4-[4-(5-{2-[(Methylsulphonyl)oxy]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}-2-oxoethyl acetateYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-[4-(5-{2-[(methylsulphonyl)oxy]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidinium chloride (500 mg) in dichloromethane (6 ml) under argon were added 2-chloro-2-oxoethyl acetate (154 mg) and triethylamine (342 mg). The reaction mixture was stirred at room temperature for 18 hours. Then water was added thereto, and it was filtered, dried and concentrated. Purification by column chromatography gave 2-{4-[4-(5-{2-[(methylsulphonyl)oxy]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}-2-oxoethyl acetate (170 mg, 30%).

Workup

  1. filtrationit was filtered
  2. customdried
  3. concentrationconcentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-04971a652d8f4c13b56059803f192286
Source dataset
uspto-grants-2016_06
Patent number
US09375009B2

Reaction notes

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