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

HRID 1080447

反応式

HRID 1080447 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 recrystallized 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 recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-466e62dee3444e54be3341b13f5e11e1
出典データセット
uspto-grants-1996_12
特許番号
US05580987

関連ノート

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