Hydrochloric Acid → HCID 66757008, compound

HRID 1642605Notes

Reaction equation

HRID 1642605 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[S:15](=[O:17])(=[O:16])[N:14]([CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:13](=[O:24])[CH2:12]2)=[C:7]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=1.[C:37]1([CH2:43][S:44](Cl)(=[O:46])=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.Cl>N1C=CC=CC=1.CCOC(C)=O>[CH2:26]([O:25][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[N:11]1[CH2:12][C:13](=[O:24])[N:14]([CH2:18][CH2:19][Si:20]([CH3:21])([CH3:22])[CH3:23])[S:15]1(=[O:16])=[O:17])[CH2:4][C:3]1[CH:33]=[CH:34][CH:35]=[CH:36][C:2]=1[NH:1][S:44]([CH2:43][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:46])=[O:45])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 74740Phenylmethanesulfonyl chlorideHCID 66757115HCID 66757115, compound

Product 1

HCID 66757008HCID 66757008, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[4-(2-aminobenzyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (150 mg, 0.29 mmol) in pyridine (3 mL) is added α-tolylsulfonyl chloride (66 mg, 0.35 mmol) and the solution is stirred at ambient temperature for 1.5 h. The mixture is neutralized using 1N HCl solution, then diluted with EtOAc. The organic phase is washed with brine and water and is dried with MgSO4, and concentrated. The residue is purified by flash column chromatography to give the title compound.

Workup

  1. washThe organic phase is washed with brine and water
  2. dry with materialis dried with MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-6fd24c6cc5f841c48d63df459219c23f
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

Loading…