Dichloromethane → 1-(n-t-Butoxycarbonyl-2(s)-aminobutyryl)-5-methoxyindoline-2(r/s)-carboxylic acid

HRID 1249934Notes

Reaction equation

HRID 1249934 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][CH3:15])[CH:11]=2)[N:6]1[C:16](=[O:28])[C@@H:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][CH3:19])=[O:4].[OH-].[Na+].ClCCl>CO.O>[C:24]([O:23][C:21]([NH:20][C@@H:17]([CH2:18][CH3:19])[C:16]([N:6]1[C:7]2[C:12](=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH2:13][CH:5]1[C:3]([OH:4])=[O:2])=[O:28])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 131723071HCID 131723071, compound

Product 1

HCID 1317230721-(n-t-Butoxycarbonyl-2(s)-aminobutyryl)-5-methoxyindoline-2(r/s)-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
7.5 °C

Procedure

To the solution of 1-(N-t-butoxycarbonyl-2(S)-aminobutyryl)-5-methoxyindoline-2(R/S)-carboxylic acid methyl ester (1.3 g, 3.3 mmol) in methanol (20 ml), was added sodium hydroxide(0.265 g, 6.6 mmol) in water (10 ml). The solution was stirred at 5 to 10° C. for 4 hours. The mixture was poured into dichloromethane (40 ml), and washed with cold potassium hydrogen sulphate (3×20 ml), and water (20 ml). The organic layer was dried over sodium sulphate, and evaporated to provide a white foam which was pure enough for the next step.

Workup

  1. washwashed with cold potassium hydrogen sulphate (3×20 ml), and water (20 ml)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated
  4. customto provide a white foam which

Sources & evidence

ORD record
ord-5400b799562a4ae3b810cabee7d83127
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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