Sodium Hydroxide → HCID 70247655, compound

HRID 1533282Notes

Reaction equation

HRID 1533282 reaction equation
C[O:2][C:3](=[O:36])[C@H:4]([CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[NH:5][C:6](=[O:25])[CH:7]([C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=1)[CH:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[OH:9].[OH-].[Na+]>CO>[CH2:23]1[O:22][C:19]2[CH:20]=[CH:21][C:16]([CH:7]([CH:8]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[OH:9])[C:6]([NH:5][C@H:4]([C:3]([OH:36])=[O:2])[CH2:26][C:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][CH:28]=3)=[O:25])=[CH:17][C:18]=2[O:24]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70248038HCID 70248038, compound

Product 1

HCID 70247655HCID 70247655, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[(2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-cyclohexyl-3-hydroxypropionyl]-L-tryptophan methyl ester (160 mg) in MeOH (2 ml) was added 1M aqueous sodium hydroxide solution (1 ml) at room temperature. After being stirred for 1 hours at the same temperature, the mixture was concentrated in vacuo. The residue was dissolved in 1N hydrochloric acid (5 ml) and ethyl acetate (10 ml) and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give N-[(2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-cyclohexyl-3-hydroxypropionyl]-L-tryptophan (150 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in 1N hydrochloric acid (5 ml)
  3. washethyl acetate (10 ml) and the organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4b3666d355b40f0865f234054dcadc8
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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