Acetyl chloride → HCID 68842039, compound

HRID 660586Notes

Reaction equation

HRID 660586 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[S:19](=[O:21])(=[O:20])[N:18]([CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:17](=[O:28])[CH2:16]2)=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:10]=1.C(N(C(C)C)CC)(C)C.[C:46](Cl)(=[O:48])[CH3:47].C(OCC)(=O)C>C(Cl)Cl>[CH2:30]([O:29][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[N:15]1[CH2:16][C:17](=[O:28])[N:18]([CH2:22][CH2:23][Si:24]([CH3:26])([CH3:27])[CH3:25])[S:19]1(=[O:21])=[O:20])[CH2:8][C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]1[NH:1][C:46](=[O:48])[CH3:47])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 68839756HCID 68839756, compound

Product 1

HCID 68842039HCID 68842039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[4-((1S*,2R*)-2-aminocyclohexylmethyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one in methylene chloride (5 mL) is added diisopropylethylamine (93 mg, 0.72 mmol) followed by acetyl chloride (36 mg, 0.458 mmol) and the mixture is stirred at RT for 24 h. Ethyl acetate is added and the mixture is washed with 1N HCl and brine. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure. The residue is purified by flash chromatography using a gradient of 25-75% EtOAc/hexane as eluent to give the title compound.

Workup

  1. washthe mixture is washed with 1N HCl and brine
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent removed under reduced pressure
  4. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-8c0186cdce32485e94e1121419028999
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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