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

HRID 1901287

Reaktionsgleichung

Reaktionsgleichung von HRID 1901287
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 19973180Phenylmethyl-[2-[(2-acetyl-1H-pyrrol-1-yl)amino]-2-oxoethyl]carbamateAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b3e9070950d54325873783a800ccf39d
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576446

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