Dicyclohexylcarbodiimide → HCID 86736753、化合物

HRID 1448572ノート

反応式

HRID 1448572 の反応式
[CH:1]([C:3]1[N:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1)=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:27]([O:30][CH2:31][C:32]1[CH2:39][S:38][CH:37]2[N:34]([C:35](=[O:41])[CH:36]2[NH2:40])[C:33]=1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])(=[O:29])[CH3:28]>O1CCCC1>[C:27]([O:30][CH2:31][C:32]1[CH2:39][S:38][CH:37]2[N:34]([C:35](=[O:41])[CH:36]2[NH:40][C:9](=[O:11])[CH2:8][N:4]2[CH:5]=[CH:6][CH:7]=[C:3]2[CH:1]=[O:2])[C:33]=1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])(=[O:29])[CH3:28]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 11771800HCID 11771800、化合物HCID 12459347(2-Formyl-1H-pyrrol-1-yl)acetic acid

生成物 1

HCID 86736753HCID 86736753、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of (2-formyl-1-pyrryl)acetic acid (3.1 g, 0.02 m) in tetrahydrofuran (THF) is cooled to about 0° C. and 4.12 g (0.02 m) of dicyclohexylcarbodiimide is added in one portion with stirring for five minutes. Then 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, tert-butyl ester (6.08 g, 0.02 m) in THF is added. The temperature is maintained at 0° C. for one hour and then the temperature is increased to 20° for about 18 hours and the solution filtered. The THF is removed at reduced pressure and the residue is taken up in ethyl acetate. The ethyl acetate is extracted with 1.0% aqueous sodium bicarbonate and water. The ethyl acetate is then filtered, dried and evaporated to give the title compound.

後処理

  1. temperaturethe temperature is increased to 20° for about 18 hours
  2. filtrationthe solution filtered
  3. customThe THF is removed at reduced pressure
  4. extractionThe ethyl acetate is extracted with 1.0% aqueous sodium bicarbonate and water
  5. filtrationThe ethyl acetate is then filtered
  6. customdried
  7. customevaporated

出典と根拠

ORDレコード
ord-fde6e25036964b97876725ebc73d7389
出典データセット
uspto-grants-1979_12
特許番号
US04180660

反応ノート

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