Dimethylformamide → HCID 19973185, compound

HRID 1451970Notes

Reaction equation

HRID 1451970 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-ec9d34944c64430e915aa23fb5594f0d
Source dataset
uspto-grants-1997_02
Patent number
US05605925

Reaction notes

Loading…