Dicyclohexylcarbodiimide → HCID 21454862, 화합물

HRID 435961노트

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HRID 435961 반응식
[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]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 11771800HCID 11771800, 화합물HCID 21454861HCID 21454861, 화합물

생성물 1

HCID 21454862HCID 21454862, 화합물수율 62.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
20 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1cded7211a68421194c57c6f2de43517
출처 데이터셋
uspto-grants-1977_02
특허 번호
US04007176

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