Diisopropylcarbodiimide → HCID 131723071, compound

HRID 1249933Notes

Reaction equation

HRID 1249933 reaction equation
[CH3:1][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)[NH:6]1)=[O:4].[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH2:28][CH3:29])[C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N=C=NC(C)C)(C)C>ClCCl>[CH3:1][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:25](=[O:26])[C@@H:24]([NH:23][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH2:28][CH3:29])=[O:4]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acidHCID 54121458(RS)-5-methoxy-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 131723071HCID 131723071, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxyindoline-2(R/S)-carboxylic acid methyl ester (1.5 g, 7.23 mmol) and N-t-butoxycarbonyl-2(S)-aminobutyric acid (1.62 g, 7.96 mmol) dissolved in dried dichloromethane (15 ml) under nitrogen at 10° C., was added diisopropylcarbodiimide (1.00 ml, 7.96 mmol). The mixture was stirred at room temperature for 24 hours, then filtered. The filtrate was evaporated under vacuum to afford a brown solid which was purified by column chromatography on silica gel using dichloromethane as eluent. A white foam was obtained which was the mixture of two diastereomers.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under vacuum
  3. customto afford a brown solid which
  4. customwas purified by column chromatography on silica gel
  5. customA white foam was obtained which
  6. additionthe mixture of two diastereomers

Sources & evidence

ORD record
ord-530a170defe74cc7bf55b8d7b8e1f327
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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