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

HRID 22403

반응식

HRID 22403 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-70557813eb5c46b0a68589cde00b35eb
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428053

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