Dicyclohexylcarbodiimide → HCID 13653509, compound

HRID 280127Notes

Reaction equation

HRID 280127 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[N:7]([NH:11][CH3:12])[CH:8]=[CH:9][CH:10]=1)=[O:5].[C:17]([O:21][C:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:12][N:11]([N:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:4](=[O:5])[C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[Cl:1])[C:26](=[O:27])[CH2:25][NH:24][C:22]([O:21][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:23]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 13457754HCID 13457754, compound

Product 1

HCID 13653509HCID 13653509, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Chlorobenzoyl)-1-methylaminopyrrole (23.7 g, 0.10 mol) and tert-butoxycarbonyl glycine (19.26 g. 0.11 mol) are combined in 250 ml of dichloromethane followed by addition of dicyclohexylcarbodiimide (23.7 g, 0.115 mol) over 3 minutes. The mixture was stirred at ambient temperature for 5 hours and thereafter filtered and evaporated to give 35 g of oil. This oil was purified by HPLC (silica, 2:1 hexane-ethyl acetate) to give 28 g of solid. This material was recrystallized from ether to give 26.5 g (68%) of cubes, m.p. 131°-133°.

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-051d8fcd2ce049be978b4c4d2e67ead2
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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