Water → HCID 18448155, compound

HRID 1269359Notes

Reaction equation

HRID 1269359 reaction equation
[C:1](=[O:34])([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][N+:31]([O-:33])=[O:32])[O:2][CH2:3]/[C:4](/[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)=[C:5](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)\[CH2:6][OH:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:37].O.OP(O)(O)=O.[O-]Cl=O.[Na+].CC(=CC)C>ClCCl.CCOC(C)=O>[CH3:23][S:20]([C:17]1[CH:18]=[CH:19][C:14](/[C:4](/[CH2:3][O:2][C:1]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][N+:31]([O-:33])=[O:32])=[O:34])=[C:5](\[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)/[C:6]([OH:37])=[O:7])=[CH:15][CH:16]=1)(=[O:21])=[O:22]

Participants

9

Reactant 6

HCID 962WaterHCID 1004Phosphoric AcidHCID 105532-Methyl-2-buteneHCID 159087TriacetoxyperiodinaneHCID 23668197Sodium ChloriteHCID 58841190HCID 58841190, compound

Product 1

HCID 18448155HCID 18448155, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl 5-(nitrooxy)pentyl carbonate (1 eq, 0.2M) in dichloromethane was treated with Dess-Martin reagent (1.3 eq) for 1 h at rt. The reaction was quenched by 10 eq of water and stirred at rt for 1 h, filtered on a silica gel pad eluted with 60% EtOAc/hexanes and evaporated. The residue was dissolved in a 3:1 solvent mixture of tBuOH/CH2Cl2, and treated with 1 M H3PO4 (4 eq) and 1 M NaClO2 (2 eq) in the presence of an excess of 2-methyl-2-butene. The resulting mixture was stirred at rt for 30 min, diluted with EtOAc and the organic layer was separated, washed with brine, dried (Na2SO4), and evaporated to afford the crude acid used as such for next step.

Workup

  1. filtrationfiltered on a silica gel pad
  2. washeluted with 60% EtOAc/hexanes
  3. customevaporated
  4. dissolutionThe residue was dissolved in a 3:1 solvent mixture of tBuOH/CH2Cl2
  5. stirringThe resulting mixture was stirred at rt for 30 min
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-3bfb3160616c4937b7f2ca1d0899226d
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

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