Pyridine → (E)-2(R)-[1(S)-(tertbutoxycarbonyl)-4-phenyl-3-butenyl]-2'-(3-chloropropylsulphonyl)-4-methylvalerohydrazide

HRID 1978085Notes

Reaction equation

HRID 1978085 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].N1C=CC=CC=1.[C:15]([O:19][C:20]([C@H:22]([C@@H:32]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:33]([NH:35][NH2:36])=[O:34])[CH2:23]/[CH:24]=[CH:25]/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>ClCCl>[C:15]([O:19][C:20]([C@H:22]([C@@H:32]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:33]([NH:35][NH:36][S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])=[O:34])[CH2:23]/[CH:24]=[CH:25]/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chlorideHCID 69709501(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide

Product 1

HCID 86756751(E)-2(R)-[1(S)-(tertbutoxycarbonyl)-4-phenyl-3-butenyl]-2'-(3-chloropropylsulphonyl)-4-methylvalerohydrazideYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.85 g of 3-chloropropylsulphonyl chloride and 0.85 g of pyridine were added to a solution of 3.0 g of (E)-2(R)-[1(S)-(tertbutoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide in 40 ml of dichloromethane. After stirring at room temperature for 2 hours the solvent was evaporated and the residue was triturated with diethyl ether. The mixture was filtered and the solvent was evaporated to give 1.92 g of (E)-2(R)-[1(S)-(tertbutoxycarbonyl)-4-phenyl-3-butenyl]-2′-(3-chloropropylsulphonyl)-4-methylvalerohydrazide in the form of a pale yellow oil.

Workup

  1. customwas evaporated
  2. customthe residue was triturated with diethyl ether
  3. filtrationThe mixture was filtered
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ba4ee019c32e4902a7a1fed66d1f201e
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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