Diisopropylcarbodiimide → HCID 131723074, compound

HRID 1249936Notes

Reaction equation

HRID 1249936 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][C:15]([F:18])([F:17])[F:16])[CH:11]=2)[NH:6]1)=[O:4].[C:19]([O:23][C:24]([NH:26][C@@H:27]([CH2:31][CH3:32])[C:28](O)=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20].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][C:15]([F:18])([F:16])[F:17])[CH:11]=2)[N:6]1[C:28](=[O:29])[C@@H:27]([NH:26][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[CH2:31][CH3:32])=[O:4]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acidHCID 76632295HCID 76632295, compound

Product 1

HCID 131723074HCID 131723074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-trifluoromethoxyindoline-2(R/S)-carboxylic acid methyl ester (1.95 g, 7.47 mmol) and N-t-butoxycarbonyl-2(S)-aminobutyric acid (1.52 g, 7.47 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 oil which was purified by column chromatography on silica gel first by using 95:5 dichloromethane: diethyl ether as eluent, then another column on silica gel by using 7:3 petroleum spirit: diethyl ether. A yellow 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 oil which
  4. customwas purified by column chromatography on silica gel first
  5. customA yellow foam was obtained which
  6. additionthe mixture of two diastereomers

Sources & evidence

ORD record
ord-a474fb13a84a45a9abc3979cae20faa7
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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