Methanol → [1,8-Diethyl-4-hydroxyimino-1,3,4,9-tetrahydro-pyrano[3.4-b]indol-1-yl]-acetic acid

HRID 399774Notes

Reaction equation

HRID 399774 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1([CH2:22][CH3:23])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[N:20][OH:21])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19].C([O-])([O-])=O.[K+].[K+].CO>O>[CH2:22]([C:5]1([CH2:4][C:3]([OH:24])=[O:2])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[N:20][OH:21])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19])[CH3:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 136365314[1,8-Diethyl-4-hydroxyimino-1,3,4,9-tetrahydro-pyrano[3.4-b]indol-1-yl]-acetic acid methyl ester

Product 1

HCID 136365313[1,8-Diethyl-4-hydroxyimino-1,3,4,9-tetrahydro-pyrano[3.4-b]indol-1-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product of Step A (0.182 g, 0.55 mmol), K2CO3 (0.1 g, 0.71 mmol) and a MeOH--H2O mixture (10 ml-1 ml) were refluxed for 3 h. The reaction mixture was cooled to room temperature and the methanol was removed. To the reaction mixture was added 10 ml H2O, which was then acidified using 1N HCl. The aqueous phase was extracted with EtOAc, which was dried (MgSO4), evaporated and triturated using hexane to yield a solid, m.p. 165°-168° C. (dec.).

Workup

  1. customthe methanol was removed
  2. additionTo the reaction mixture was added 10 ml H2O, which
  3. extractionThe aqueous phase was extracted with EtOAc, which
  4. dry with materialwas dried (MgSO4)
  5. customevaporated
  6. customtriturated
  7. customto yield a solid, m.p. 165°-168° C. (dec.)

Sources & evidence

ORD record
ord-45987971c229458787ef945731ae4705
Source dataset
uspto-grants-1998_10
Patent number
US05824699

Reaction notes

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