Pyridine → (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methyl-2'-(2-nitrobenzylsulphonyl)valerohydrazide

HRID 1386560Notes

Reaction equation

HRID 1386560 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([NH:24][NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].[N+:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][S:44](Cl)(=[O:46])=[O:45])([O-:36])=[O:35].N1C=CC=CC=1>ClCCl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([NH:24][N:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[S:44]([CH2:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[N+:34]([O-:36])=[O:35])(=[O:45])=[O:46])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4305447(2-nitrophenyl)methanesulfonyl ChlorideHCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86757177(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methyl-2'-(2-nitrobenzylsulphonyl)valerohydrazideYield 109.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.689 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS) -pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 8 ml of dichloromethane was treated with 0.236 g of 2-nitro-α-toluenesulphonyl chloride and 0.152 ml of pyridine at room temperature and under a nitrogen atmosphere. The mixture was stirred for 2 hours and evaporated. The residue was dissolved in ethyl acetate and washed in sequence with water, 5% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulphate. Evaporation and trituration of the residue with diethyl ether gave 0.72 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(2-nitrobenzylsulphonyl)valerohydrazide in the form of a white solid.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed in sequence with water, 5% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customEvaporation and trituration of the residue with diethyl ether

Sources & evidence

ORD record
ord-706e871b77c940c7ba4266c8f3ea18b7
Source dataset
uspto-grants-2001_07
Patent number
US06265446B1

Reaction notes

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