p-Toluenesulfonic acid → HCID 86756871, compound

HRID 1979188Notes

Reaction equation

HRID 1979188 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:22]([NH:24][N:25]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:26](=[O:35])[C@@H:27]([CH2:29][O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[NH2:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].[C:44]1([CH3:54])[CH:49]=[CH:48][C:47]([S:50]([OH:53])(=[O:52])=[O:51])=[CH:46][CH:45]=1>CO>[C:44]1([CH3:54])[CH:45]=[CH:46][C:47]([S:50]([OH:53])(=[O:51])=[O:52])=[CH:48][CH:49]=1.[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:22]([NH:24][N:25]([CH2:36][CH:37]([CH3:38])[CH3:39])[C:26](=[O:35])[C@@H:27]([CH2:29][O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[NH2:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86756873HCID 86756873, compound

Product 1

HCID 86756871HCID 86756871, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.38 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-2′-(O-tert.butyl-D-seryl)-4-methylvalerohydrazide in 5 ml of methanol was treated with 0.144 g of p-toluenesulphonic acid. The mixture was stirred for 3.5 hours at room temperature and evaporated to give a solid. This was triturated with diethyl ether, filtered off and dried to give 0.38 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-2′-(O-tert.butyl-D-seryl)-4-methylvalerohydrazide p-toluenesulphonate in the form of a white solid.

Workup

  1. customevaporated
  2. customto give a solid
  3. customThis was triturated with diethyl ether
  4. filtrationfiltered off
  5. customdried

Sources & evidence

ORD record
ord-cf114a85aabd413e9293732d0d985809
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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