Dicyclohexylcarbodiimide → HCID 21454862、化合物

HRID 435961ノート

反応式

HRID 435961 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:15])[CH:10]2[NH2:14])[C:7]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[S:38]1[CH2:43][CH2:42][S:41][CH:40]=[C:39]1[CH2:44][C:45](O)=[O:46]>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:15])[CH:10]2[NH:14][C:45](=[O:46])[CH2:44][C:39]2[S:38][CH2:43][CH2:42][S:41][CH:40]=2)[C:7]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 11771800HCID 11771800、化合物HCID 21454861HCID 21454861、化合物

生成物 1

HCID 21454862HCID 21454862、化合物収率 62.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

3-Acetoxymethyl-7-amino-2(t-butoxycarbonyl)-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (11.2 g.) and dicyclohexylcarbodiimide (7.8 g.) are added to a solution of (5,6-dihydro-1,4-dithiin-2-yl)acetic acid (6 g.) in dimethylformamide (50 cc.). The reagents are left in contact for 5 hours, with stirring, at a temperature of about 20° C. and then the solid is filtered off. The filtrate is taken up in ethyl acetate (300 cc.) and is washed with an aqueous solution of sodium bicarbonate, N hydrochloric acid and then with water. After drying over sodium sulphate, it is treated with decolourizing charcoal and concentrated to dryness under reduced pressure (20 mm.Hg). A residue (20 g.) is obtained and is chromatographed on silica (330 g.). Elution is effected using a mixture (10 liters) of ethyl acetate and cyclohexane (1-3 by volume), and the eluates are concentrated to dryness under reduced pressure (20 mm.Hg). 3-Acetoxymethyl-2-(t-butoxycarbonyl)-7-[(5,6-dihydro-1,4-dithiin-2 -yl)acetamido]-8-oxo-5-thia-1 -aza-bicyclo-[4,2,0]oct-2-ene (10.3 g.), melting at 80° C., is thus obtained.

後処理

  1. filtrationthe solid is filtered off
  2. washis washed with an aqueous solution of sodium bicarbonate, N hydrochloric acid
  3. dry with materialAfter drying over sodium sulphate, it
  4. additionis treated with decolourizing charcoal
  5. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)
  6. customA residue (20 g.) is obtained
  7. customis chromatographed on silica (330 g.)
  8. washElution
  9. concentrationthe eluates are concentrated to dryness under reduced pressure (20 mm.Hg)

出典と根拠

ORDレコード
ord-1cded7211a68421194c57c6f2de43517
出典データセット
uspto-grants-1977_02
特許番号
US04007176

反応ノート

読み込み中…