Methanol → HCID 69421115, compound

HRID 1375622Notes

Reaction equation

HRID 1375622 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][C@H:13]([C@H:15]1[CH2:19][O:18]C(C)(C)N1C(OC(C)(C)C)=O)[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][C:30]([CH3:32])=[O:31].OS(O)(=O)=O.O=[Cr](=O)=O.[C:42](=[O:45])(O)[O-:43].[Na+].[CH3:47]O>CC(C)=O>[CH2:1]([O:8][C:9]([CH2:11][CH2:12][C@@H:13]([CH3:14])[C@H:15]([C:19]([O:31][C:30]([CH3:47])([CH3:32])[CH3:29])=[O:18])[C:42]([OH:43])=[O:45])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 69118652HCID 69118652, compoundHCID 131709961Jones' reagent

Product 1

HCID 69421115HCID 69421115, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the product from step d (130 mg) in acetone (7 mL) was added Jones' reagent (1.0 mL) at 0° C. The mixture, while stirring, was allowed warm from 0° C. to rt. for 1 hr. Sodium bicarbonate and methanol were added, and the solvent was evaporated. The crude product was purified by reverse phase HPLC purification (acetonitrile/water 30% to 100% gradient) to provide (2S,3R)-5-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)-3-methylpentanoic acid as a clear oil. LC-MS found: (M+1)+=506.40.

Workup

  1. temperaturewas allowed warm from 0° C. to rt
  2. customthe solvent was evaporated
  3. customThe crude product was purified by reverse phase HPLC purification (acetonitrile/water 30% to 100% gradient)

Sources & evidence

ORD record
ord-8835d3618cd044488029d3813fddfb83
Source dataset
uspto-grants-2007_01
Patent number
US07169795B2

Reaction notes

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