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

HRID 1901287

反応式

HRID 1901287 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b3e9070950d54325873783a800ccf39d
出典データセット
uspto-grants-1996_11
特許番号
US05576446

関連ノート

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