Diisopropylcarbodiimide → HCID 54025075, compound

HRID 1249918Notes

Reaction equation

HRID 1249918 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:14])[CH:11]=2)[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]([C@@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:14])[CH:11]=2)[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 22451271HCID 22451271, compound

Product 1

HCID 54025075HCID 54025075, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloroindoline-2(R/S)-carboxylic acid methyl ester (1.2 g, 5.69 mmol) and N-t-butoxycarbonyl-2(S)-aminobutyric acid (1.27 g, 6.25 mmol) dissolved in dried dichloromethane (10 ml) under nitrogen at 10° C., was added diisopropylcarbodiimide (0.98 ml, 6.30 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 20:1 dichloromethane: diethyl ether as eluent. A white foam was obtained which was the mixture of two diastereomers. The two diastereomers were separated by column chromatography on silica gel using 7:3 petroleum spirit:diethyl ether as eluent, and the pure (S,S) form was obtained as a white foam.

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 20:1 dichloromethane
  5. customA white foam was obtained which
  6. additionthe mixture of two diastereomers
  7. customThe two diastereomers were separated by column chromatography on silica gel using 7:3 petroleum spirit
  8. customdiethyl ether as eluent, and the pure (S,S) form was obtained as a white foam

Sources & evidence

ORD record
ord-38dfaf71bbbe4dfeba03b0df7ca7bec0
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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