Dicyclohexylcarbodiimide → Phenylmethyl-[2-[(3-benzoyl-1H-pyrrol-1-yl)amino]-2-oxoethyl]carbamate

HRID 1080474Notes

Reaction equation

HRID 1080474 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:3]1.[C:15]([NH:25][CH2:26][C:27](O)=[O:28])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C)C=O>[C:19]1([CH2:18][O:17][C:15](=[O:16])[NH:25][CH2:26][C:27]([NH:1][N:2]2[CH:6]=[CH:5][C:4]([C:7](=[O:8])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:3]2)=[O:28])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 199731561-Amino-3-benzoylpyrrole

Product 1

HCID 19973189Phenylmethyl-[2-[(3-benzoyl-1H-pyrrol-1-yl)amino]-2-oxoethyl]carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-amino-1H-pyrrol-3-yl)phenylmethanone (5.96 g) and N-carbobenzyloxyglycine (6.69 g) in 70 ml of anhydrous DCM and 30 ml of anhydrous dimethylformamide was added DCC (7.22 g). The reaction mixture was stirred at room temperature for 4 hours and filtered. The filter cake was washed with ethyl acetate, and the combined filtrates were evaporated in vacuo. The residual oil was purified by preparative HPLC (silica gel, DCM/ethyl acetate 3:1). Evaporation of the desired fractions afforded a colorless oil, which was crystallized from DCM/ethyl ether yielding the product as colorless crystals (5.96 g), m.p. 144°-145° C.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with ethyl acetate
  3. customthe combined filtrates were evaporated in vacuo
  4. customThe residual oil was purified by preparative HPLC (silica gel, DCM/ethyl acetate 3:1)
  5. customEvaporation of the desired fractions
  6. customafforded a colorless oil, which
  7. customwas crystallized from DCM/ethyl ether yielding the product as colorless crystals (5.96 g), m.p. 144°-145° C.

Sources & evidence

ORD record
ord-84ee783b54b0491b93e4c26cb047146c
Source dataset
uspto-grants-1996_12
Patent number
US05580987

Reaction notes

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