Methanol → HCID 19710734, compound

HRID 2395441Notes

Reaction equation

HRID 2395441 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-34c09c0e02b44f12942c6cd32b0745c8
Source dataset
uspto-grants-1998_09
Patent number
US05814653

Reaction notes

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