Acetyl chloride → N-(3-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propyl)-acetamide

HRID 660536Notes

Reaction equation

HRID 660536 reaction equation
[OH:1][C:2]([C:4](F)(F)F)=O.[NH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[S:22](=[O:24])(=[O:23])[N:21]([CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:20](=[O:31])[CH2:19]2)=[C:14]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:13]=1.C(N(C(C)C)CC)(C)C.C(Cl)(=O)C>C(Cl)Cl>[CH2:33]([O:32][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][CH2:9][NH:8][C:2](=[O:1])[CH3:4])[CH:17]=[CH:16][C:15]=1[N:18]1[CH2:19][C:20](=[O:31])[N:21]([CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])[S:22]1(=[O:24])=[O:23])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 866325735-[4-(3-Aminopropyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one TFA Salt

Product 1

HCID 68843471N-(3-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[4-(3-aminopropyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one TFA salt (124 mg, 0.26 mmol) in methylene chloride (5 mL) is added diisopropylethylamine (0.1 mg, 0.781 mmol) then acetyl chloride (21 mg, 0.267 mmol) and the mixture is stirred at RT for 18 h. The solvent is removed under reduced pressure and 1 N HCl is added. The mixture is extracted with ether and the organic phase is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using a gradient of 10-50% EtOAc/hexane as eluent to give the title compound.

Workup

  1. customThe solvent is removed under reduced pressure and 1 N HCl
  2. additionis added
  3. extractionThe mixture is extracted with ether
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-bd85c901259849a79c8a77c73d7c6151
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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