Water → HCID 131723064, compound

HRID 1249923Notes

Reaction equation

HRID 1249923 reaction equation
C[O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=2)[N:6]1[C:22](=[O:34])[C@@H:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24][CH3:25])=[O:4].O.[OH-].[Na+].ClCCl>CO>[C:30]([O:29][C:27]([NH:26][C@@H:23]([CH2:24][CH3:25])[C:22]([N:6]1[C:7]2[C:12](=[CH:11][C:10]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:9][CH:8]=2)[CH2:13][CH:5]1[C:3]([OH:4])=[O:2])=[O:34])=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 131723065HCID 131723065, compound

Product 1

HCID 131723064HCID 131723064, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(N-t-butoxycarbonyl-2(S)-aminobutyryl)-5-benzyloxyindoline-2(R/S)-carboxylic acid methylester (2.75 g, 5.76 mmol) in methanol (20 mL), was added the water solution of sodium hydroxide (0.46 g, 11.52 mmol) under nitrogen at 10-15° C. The solution was stirred at room temperature for fourteen hours, then poured into dichloromethane and washed with potassium hydrogen sulphate solution, water. The organic layer was separated and dried over magnesium sulphate, solvent removal gave a yellow foam which was pure enough for the next step.

Workup

  1. washwashed with potassium hydrogen sulphate solution, water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulphate, solvent removal
  4. customgave a yellow foam which

Sources & evidence

ORD record
ord-5ce1a3227b164c3187b0bd473ea7ce8e
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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