p-Toluenesulfonic acid → HCID 86756736, compound

HRID 1978072Notes

Reaction equation

HRID 1978072 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:24]([CH2:39][CH:40]([CH3:42])[CH3:41])[C:25]([NH:27][N:28]([S:35]([CH3:38])(=[O:37])=[O:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.ClCCl>[OH:7][NH:8][C:9]([C@H:11]([C@@H:24]([CH2:39][CH:40]([CH3:42])[CH3:41])[C:25]([NH:27][N:28]([S:35]([CH3:38])(=[O:37])=[O:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:10]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86756737HCID 86756737, compound

Product 1

HCID 86756736HCID 86756736, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.080 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-(4-nitrophenyl)-3-butenyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in a mixture of 3 ml of methanol and 1.5 ml of dichloromethane was treated with 0.020 g of 4-toluenesulphonic acid. The mixture was stirred for 5 hours at room temperature and the solution was evaporated. The resulting gum was triturated with diethyl ether to give 0.063 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-(4-nitrophenyl)-3-butenyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in the form of a light-brown solid.

Workup

  1. customthe solution was evaporated
  2. customThe resulting gum was triturated with diethyl ether

Sources & evidence

ORD record
ord-22d548c3cbcc4db0bd83495f856799a5
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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