Dicyclohexylcarbodiimide → HCID 13457756, compound

HRID 280128Notes

Reaction equation

HRID 280128 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14].[C:16]([O:20][C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]([NH:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 13457740HCID 13457740, compound

Product 1

HCID 13457756HCID 13457756, compoundYield 143.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Amino-2-(2-chlorobenzoyl)pyrrole (24.3 g, 0.12 mol) and t-butoxycarbonyl glycine (22.7 g, 0.13 mol) were dissolved in 300 ml of dichloromethane. Dicyclohexylcarbodiimide (26.8 g, 0.13 mol) was added over 3 minutes and the reaction mixture stirred at ambient temperature for 4 hours. The resultant slurry was filtered, and the the filtrate evaporated to give 65 g of oil. This oil was purified by flash chromatography (silica, 2:1 hexane-ethyl acetate) to give 21.9 g (48%) of cystals, m.p. 156°-158°.

Workup

  1. filtrationThe resultant slurry was filtered
  2. customthe the filtrate evaporated

Sources & evidence

ORD record
ord-9e864f1d076a402cbc91a8cb0d0698bc
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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