Acetyl chloride → 5-{4-[(E)-2-(1-Acetylpiperidin-2-yl)-vinyl]-2-benzyloxyphenyl}-1,1-dioxo-2-(2-trimethylsilanyl-ethyl)-1,2,5-thiadiazolidin-3-one

HRID 660584Notes

Reaction equation

HRID 660584 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][NH:18]2)[CH:12]=[CH:11][C:10]=1[N:23]1[S:27](=[O:29])(=[O:28])[N:26]([CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:25](=[O:36])[CH2:24]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:44](Cl)(=[O:46])[CH3:45]>C(Cl)Cl.CCOC(C)=O>[C:44]([N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1/[CH:16]=[CH:15]/[C:13]1[CH:12]=[CH:11][C:10]([N:23]2[S:27](=[O:28])(=[O:29])[N:26]([CH2:30][CH2:31][Si:32]([CH3:34])([CH3:33])[CH3:35])[C:25](=[O:36])[CH2:24]2)=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=1)(=[O:46])[CH3:45]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68842724HCID 68842724, compound

Product 1

HCID 688392285-{4-[(E)-2-(1-Acetylpiperidin-2-yl)-vinyl]-2-benzyloxyphenyl}-1,1-dioxo-2-(2-trimethylsilanyl-ethyl)-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[2-benzyloxy-4-((E)-2-piperidin-2-yl-vinyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (101 mg, 0.192 mmol) in methylene chloride (4 mL) is added triethylamine (0.134 mL, 0.956 mmol). The solution is stirred at RT for 5 min the acetyl chloride (0.0163 mL, 0.23 mmol) is added and stirring is continued for 18 h. The mixture is diluted with EtOAc and is washed with 1N HCl and brine. The organic phase is dried over sodium sulfate and the solvent removed under reduced pressure to give the title compound.

Workup

  1. additionis added
  2. washis washed with 1N HCl and brine
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a89b8e5d94144df08747dc62ac33f84d
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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