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

HRID 1451955

反応式

HRID 1451955 の反応式
[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

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 1365891-Aminopyrrole

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fb7223447aeb45bd9db3c60fe24be589
出典データセット
uspto-grants-1997_02
特許番号
US05605925

関連ノート

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