2-Thiophenesulfonyl chloride → HCID 69943566, compound

HRID 1978062Notes

Reaction equation

HRID 1978062 reaction equation
[NH2:1][CH2:2][C@@H:3]([C@@H:11]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:12]([NH:14][N:15]([S:22]([CH3:25])(=[O:24])=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[S:35](Cl)(=[O:37])=[O:36]>ClCCl>[C:7]([O:6][C:4]([C@H:3]([C@@H:11]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:12]([NH:14][N:15]([S:22]([CH3:25])(=[O:24])=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:2][NH:1][S:35]([C:31]1[S:30][CH:34]=[CH:33][CH:32]=1)(=[O:37])=[O:36])=[O:5])([CH3:9])([CH3:10])[CH3:8]

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 69942786HCID 69942786, compound

Product 1

HCID 69943566HCID 69943566, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.504 g of 2(R)-[2-amino-1(R)-(tert-butoxycarbonyl)ethyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in 20 ml of dichloromethane was cooled to 0° C. while stirring and 0.242 g of 2-thiophenesulphonyl chloride was added. The mixture was left to come to room temperature and was stirred overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate and 5% aqueous citric acid solution. The ethyl acetate layer was washed with saturated sodium hydrogen carbonate solution and then with saturated sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated. The residue was triturated with ether and there was obtained 0.487 g of 2(R)-[1(R)-(tert-butoxycarbonyl)-2-[(2-thienyl)sulphonamido]ethyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in the form of a white solid.

Workup

  1. waitThe mixture was left
  2. customto come to room temperature
  3. stirringwas stirred overnight
  4. customThe solvent was evaporated
  5. customthe residue was partitioned between ethyl acetate and 5% aqueous citric acid solution
  6. washThe ethyl acetate layer was washed with saturated sodium hydrogen carbonate solution
  7. dry with materialwith saturated sodium chloride solution, dried over anhydrous magnesium sulphate
  8. customevaporated
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-7ed516c771f340fa9c506c347900864e
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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