Methanol → HCID 19710734, compound

HRID 843888Notes

Reaction equation

HRID 843888 reaction equation
[CH2:1]([CH:3]1[C:15]2[NH:14][C:13]3[CH:12]=[CH:11][C:10](OCC4C=CC=CC=4)([O:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:9][C:8]=3[C:7]=2[CH2:6][CH:5]([C:32]([OH:34])=[O:33])[CH2:4]1)[CH3:2].CO>[OH-].[Na+]>[CH2:1]([CH:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][C:10]([O:16][CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:11][CH:12]=3)[C:7]=2[CH2:6][CH:5]([C:32]([OH:34])=[O:33])[CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 70155146HCID 70155146, compound

Product 1

HCID 19710734HCID 19710734, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a suspension of 3.107 gm (8.9 mMol) ethyl 6-benzyloxy-3-carboxy-6-benzyloxy-1,2,3,4-tetrahydro-9H-carbazole in 100 mL 2N sodium hydroxide were added 100 mL methanol and the reaction mixture stirred at reflux for 3.5 hours. The reaction mixture was concentrated to about half volume and the pH adjusted to between 5 and 7 by the addition of concentrated hydrochloric acid. The mixture was extracted well with 4:1 dichloromethane:isopropanol. The organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure to give 2.71 gm (95%) of the title compound.

Workup

  1. temperatureat reflux for 3.5 hours
  2. concentrationThe reaction mixture was concentrated to about half volume
  3. additionthe pH adjusted to between 5 and 7 by the addition of concentrated hydrochloric acid
  4. extractionThe mixture was extracted well with 4:1 dichloromethane
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a285df74f88c46cb8ea7d7ef639e8d4d
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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