Methanesulfonic Acid → HCID 9955564, compound

HRID 1978064Notes

Reaction equation

HRID 1978064 reaction equation
O1CCCCC1[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][S:26]([CH3:29])(=[O:28])=[O:27])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].CS(O)(=O)=O>CO.ClCCl>[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:22]([NH:24][N:25]([CH2:9][CH:11]([CH3:21])[CH3:12])[S:26]([CH3:29])(=[O:28])=[O:27])=[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 2

HCID 6395Methanesulfonic AcidHCID 86756723HCID 86756723, compound

Product 1

HCID 9955564HCID 9955564, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.246 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-(methanesulphonyl)-4-methylvalerohydrazide in a mixture of 10 ml of methanol and 2 ml of dichloromethane was treated with 0.006 ml of methanesulphonic acid. The mixture was stirred for 3 hours at room temperature and then the solvent was evaporated. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was dried over anhydrous magnesium sulphate and the solvent evaporated. The residue was triturated with hexane to give 0.119 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulphate
  4. customthe solvent evaporated
  5. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-3ed720023d49433e976eca424d5769bf
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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