Dimethylformamide → HCID 19973185, compound

HRID 22395Notes

Reaction equation

HRID 22395 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([C:9]1[NH:10][CH:11]=[CH:12][CH:13]=1)=[O:8].[C:14]([NH:24]NCC(O)=O)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C1CCC(N=C=N[CH:39]2[CH2:44]CCCC2)CC1.CN(C)C=[O:48]>C(Cl)Cl>[C:18]1([CH2:17][O:16][C:14](=[O:15])[NH:24][CH2:39][C:44](=[O:48])[NH:1][N:2]2[CH:6]=[CH:5][CH:4]=[C:3]2[C:7]([C:9]2[NH:10][CH:11]=[CH:12][CH:13]=2)=[O:8])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 19973150HCID 19973150, compoundHCID 19973212HCID 19973212, compound

Product 1

HCID 19973185HCID 19973185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-amino-1H-pyrrol-2-yl)-1H-pyrrol-2-ylmethanone (4.41 g) and N-carbobenzyloxyaminoglycine (5.27 g) in 10 ml of anhydrous dimethylformamide and 100 ml of anhydrous DCM was added DCC (6.23 g). The reaction mixture was stirred overnight at room temperature, filtered and the filtrate evaporated in vacuo. The residual oil was purified by preparative HPLC (n-heptane/ethyl acetate 2:3) and subsequent recrystallization from ethyl acetate/n-heptane afforded the product as a powder (6.74 g), m.p. 157°-158° C.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated in vacuo
  3. customThe residual oil was purified by preparative HPLC (n-heptane/ethyl acetate 2:3) and subsequent recrystallization from ethyl acetate/n-heptane

Sources & evidence

ORD record
ord-47eef77a8972422ea9baffbc5609e04f
Source dataset
uspto-grants-1995_06
Patent number
US05428053

Reaction notes

Loading…