Dicyclohexylcarbodiimide → Phenylmethyl-[2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

HRID 1451955

반응식

HRID 1451955 반응식
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[C:7]([NH:17][CH2:18][C:19](O)=[O:20])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C)C=O>[C:11]1([CH2:10][O:9][C:7](=[O:8])[NH:17][CH2:18][C:19](=[O:20])[NH:1][N:2]2[CH:6]=[CH:5][CH:4]=[CH:3]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 1365891-Aminopyrrole

생성물 1

HCID 19973152Phenylmethyl-[2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate수율 18.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-aminopyrrole (2.46 g) and carbobenzyloxyglycine (6.28 g) in 120 ml of dry DCM and 10 ml of dry dimethylformamide was added DCC (8.00 g). The reaction mixture was stirred at room temperature over a period of 64 hours. The precipitate was removed by filtration and stirred in boiling ethyl acetate. The mixture was filtered and the filtrate was combined with the filtrate of the reaction mixture and evaporated to dryness. The residue was purified by flash column chromatography (silica gel, DCM/methanol 20:1) yielding a first fraction (2.97 g) which was contaminated by DCU. A second fraction re, crystallized from ethyl acetate afforded 1.54 g of the product as crystals, m.p. 146°-147° C.

후처리

  1. customThe precipitate was removed by filtration
  2. stirringstirred
  3. filtrationThe mixture was filtered
  4. customevaporated to dryness
  5. customThe residue was purified by flash column chromatography (silica gel, DCM/methanol 20:1)
  6. customyielding a first fraction (2.97 g) which
  7. customA second fraction re, crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-fb7223447aeb45bd9db3c60fe24be589
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05605925

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