Dicyclohexylcarbodiimide → Phenylmethyl-[2-[(3-benzoyl-1H-pyrrol-1-yl)amino]-2-oxoethyl]carbamate

HRID 22408

反応式

HRID 22408 の反応式
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:3]1.[C:15]([NH:25][CH2:26][C:27](O)=[O:28])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C)C=O>[C:19]1([CH2:18][O:17][C:15](=[O:16])[NH:25][CH2:26][C:27]([NH:1][N:2]2[CH:6]=[CH:5][C:4]([C:7](=[O:8])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:3]2)=[O:28])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 199731561-Amino-3-benzoylpyrrole

生成物 1

HCID 19973189Phenylmethyl-[2-[(3-benzoyl-1H-pyrrol-1-yl)amino]-2-oxoethyl]carbamate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (1-amino-1H-pyrrol-3-yl)phenylmethanone (5.96 g) and N-carbobenzyloxyglycine (6.69 g) in 70 ml of anhydrous DCM and 30 ml of anhydrous dimethylformamide was added DCC (7.22 g). The reaction mixture was stirred at room temperature for 4 hours and filtered. The filter cake was washed with ethyl acetate, and the combined filtrates were evaporated in vacuo. The residual oil was purified by preparative HPLC (silica gel, DCM/ethyl acetate 3:1). Evaporation of the desired fractions afforded a colorless oil, which was crystallized from DCM/ethyl ether yielding the product as colorless crystals (5.96 g), m.p. 144°-145° C.

後処理

  1. filtrationfiltered
  2. washThe filter cake was washed with ethyl acetate
  3. customthe combined filtrates were evaporated in vacuo
  4. customThe residual oil was purified by preparative HPLC (silica gel, DCM/ethyl acetate 3:1)
  5. customEvaporation of the desired fractions
  6. customafforded a colorless oil, which
  7. customwas crystallized from DCM/ethyl ether yielding the product as colorless crystals (5.96 g), m.p. 144°-145° C.

出典と根拠

ORDレコード
ord-489d0133ade44cc9bcb67c29672dfe80
出典データセット
uspto-grants-1995_06
特許番号
US05428053

関連ノート

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