Methanol → HCID 57791947, compound

HRID 1686442Notes

Reaction equation

HRID 1686442 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])=[CH:15][C:14]=2[Cl:24])[CH:6]=1.CO.[Si](C=[N+]=[N-])(C)(C)[CH3:29]>C1(C)C=CC=CC=1>[Cl:24][C:14]1[CH:15]=[C:16]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH:17]=[CH:18][C:13]=1[O:12][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:25])[CH:10]=[C:9]([O:11][CH3:29])[CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 131729542HCID 131729542, compound

Product 1

HCID 57791947HCID 57791947, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product from step (i) was taken up in toluene (3 ml) and methanol (1 ml) and TMS-diazomethane (0.6 ml, 2M in diethylether) added, the mixture stirred at RT for 3 h then evaporated under reduced pressure. The residue was taken up in THF (2 ml) and methanol (1 ml) then 3M NaOH (2 ml) added and the mixture stirred at RT for 2 h. The mixture was then acidified to pH 2 and extracted with ethyl acetate. The organics were dried (MgSO4), evaporated under reduced pressure and then passed onto a Varian NH2 resin (eluting with ethyl acetate, acetonitrile, methanol, DCM then 20% acetic acid in DCM). The acidic fraction was evaporated under reduced pressure and then purified by RPHPLC to give a white solid.

Workup

  1. customthen evaporated under reduced pressure
  2. additionmethanol (1 ml) then 3M NaOH (2 ml) added
  3. stirringthe mixture stirred at RT for 2 h
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organics were dried (MgSO4)
  6. customevaporated under reduced pressure
  7. washeluting with ethyl acetate, acetonitrile, methanol, DCM
  8. customThe acidic fraction was evaporated under reduced pressure
  9. custompurified by RPHPLC
  10. customto give a white solid

Sources & evidence

ORD record
ord-8b5e0b8489a54c8499a57c9756747d84
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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