Methanol → HCID 11666861, compound

HRID 229754Notes

Reaction equation

HRID 229754 reaction equation
[O:1]=[C:2]1[NH:6][C@@H:5]([CH2:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12]2[C:17](=[O:21])[O:18][CH2:19][CH2:20][C:11]3=2)[CH2:4][O:3]1.CS(O)(=O)=O.[CH3:27][OH:28]>>[CH3:27][O:28][C:17]([C:12]1[NH:13][C:14]2[C:10]([C:11]=1[CH2:20][CH2:19][OH:18])=[CH:9][C:8]([CH2:7][C@H:5]1[CH2:4][O:3][C:2](=[O:1])[NH:6]1)=[CH:16][CH:15]=2)=[O:21]

Participants

4

Reactant 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 9994130HCID 9994130, compound

Product 1

HCID 11666861HCID 11666861, compoundYield 93%

Procedure

To a suspension of 500 mg (1.74 mmoles) of the (S)-6-(2-oxo-1,3-oxazolidin-4-ylmethyl)-4,9-dihydro-3H-pyrano-[3,4-b]indol-1-one in 10 ml of methanol were added 0.12 ml (1.9 mmoles) of methanesulphonic acid. The mixture was left under stirring at the reflux temperature for 3 hours. The solvent was evaporated to dryness under reduced pressure, the residue dissolved with 10 ml of a saturated bicarbonate solution and extracted three times with dichloromethane. The combined organic phases were dried and evaporated to dryness and the evaporated solid recrystallised from ethanol to give 517 mg (93%) of the title ester as a yellow crystalline solid.

Workup

  1. waitThe mixture was left
  2. customThe solvent was evaporated to dryness under reduced pressure
  3. dissolutionthe residue dissolved with 10 ml of a saturated bicarbonate solution
  4. extractionextracted three times with dichloromethane
  5. customThe combined organic phases were dried
  6. customevaporated to dryness
  7. customthe evaporated solid recrystallised from ethanol

Sources & evidence

ORD record
ord-cf805fa0cc3c474aba8b49350e6c5436
Source dataset
uspto-grants-2009_07
Patent number
US07563904B2

Reaction notes

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