Dimethylformamide → HCID 19973185, compound

HRID 1901281Notes

Reaction equation

HRID 1901281 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-d3d248d478494dedabae8362f864f33a
Source dataset
uspto-grants-1996_11
Patent number
US05576446

Reaction notes

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