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

HRID 327840

Reaction equation

HRID 327840 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:9])[CH3:8].[C:10]([NH:20][CH2:21][C:22](O)=[O:23])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:14]1([CH2:13][O:12][C:10](=[O:11])[NH:20][CH2:21][C:22]([NH:1][N:2]2[CH:6]=[CH:5][CH:4]=[C:3]2[C:7](=[O:9])[CH3:8])=[O:23])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 199667441-(1-Amino-1H-pyrrol-2-yl)ethanone

Product 1

HCID 19973180Phenylmethyl-[2-[(2-acetyl-1H-pyrrol-1-yl)amino]-2-oxoethyl]carbamateYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution consisting of 1-(1-amino-1H-pyrrol-2-yl)ethanone (3.88 g) and carbobenzyloxyglycine (6.54 g) in dry DCM (115 ml) was added DCC (6.77 g) at 0° C. under nitrogen. The reaction mixture was allowed to stir at room temperature for 18 hours. The precipitated DCU was removed by filtration and washed with ethyl acetate. The combined filtrates were concentrated to give the crude product. Purification via flash column chromatography (silica gel, 10% EtOAc/hexane) afforded 6.98 g of the product as a solid, m.p. 109°-111° C.

Workup

  1. customThe precipitated DCU was removed by filtration
  2. washwashed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated
  4. customto give the crude product
  5. customPurification via flash column chromatography (silica gel, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-a2ce4ab2ee5648b8aa98293e8ffcff04
Source dataset
uspto-grants-1993_12
Patent number
US05274116

Linked notes

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