Diisopropylcarbodiimide → HCID 131723070, compound

HRID 1249931Notes

Reaction equation

HRID 1249931 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[F:14])[NH:6]1)=[O:4].[C:15]([O:19][C:20]([NH:22][C@@H:23]([CH2:27][CH3:28])[C:24](O)=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16].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]=[CH:10][C:11]=2[F:14])[N:6]1[C:24](=[O:25])[C@@H:23]([NH:22][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH2:27][CH3:28])=[O:4]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acidHCID 76453899HCID 76453899, compound

Product 1

HCID 131723070HCID 131723070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoroindoline-2(R/S)-carboxylic acid methyl ester (0.43 g, 2.205 mmol) and N-t-butoxycarbonyl-2(S)-aminobutyric acid (0.47 g, 2.33 mmol) dissolved in dried dichloromethane(10 ml) under nitrogen at 10° C., was added diisopropylcarbodiimide (0.36 ml, 2.33 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 10:1 dichloromethane: diethyl ether as eluent. An off-white foam was obtained which was the mixture of the 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 using 10:1 dichloromethane
  5. customAn off-white foam was obtained which
  6. additionthe mixture of the two diastereomers

Sources & evidence

ORD record
ord-c579b1ad565645bf88dcfa5c95d0bfa2
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

Loading…