Water → HCID 69959107, compound

HRID 411991Notes

Reaction equation

HRID 411991 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([OH:12])[CH2:9][C@H:8]1[C:13]([OH:15])=[O:14])=[O:6])[CH:2]=[CH2:3].OS(O)(=O)=O.O>CC(C)=O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C:10](=[O:12])[CH2:9][C@H:8]1[C:13]([OH:15])=[O:14])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 57167302HCID 57167302, compound

Product 1

HCID 69959107HCID 69959107, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The alloc protected hydroxy proline (13) (18 g, 83.72 mmol) was dissolved in acetone (1260 ml). The Jone's reagent [Cro3:26.6 g/H2SO4:21.3 ml and the solution was made up to 100 ml with water] (87 ml) was added over 10 min. The resulting mixture was stirred for a further 45 minutes when the excess oxidant was quenched with methanol (15 ml). The green chromium salts were removed by filtration through Celite and the filtrate was diluted in CHCl3(1000 ml). The combined organic phase was washed with brine several times (5×500 ml) and the solvent was evaporated under reduced pressure, to yield the ketone 14 which was used without any purification.

Workup

  1. additionwas added over 10 min
  2. customwas quenched with methanol (15 ml)
  3. customThe green chromium salts were removed by filtration through Celite
  4. additionthe filtrate was diluted in CHCl3(1000 ml)
  5. washThe combined organic phase was washed with brine several times (5×500 ml)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f2eb86c16d8848deabe343ba1401cb7d
Source dataset
uspto-grants-2003_05
Patent number
US06562806B1

Reaction notes

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