Water → Diisopropyl Ether

HRID 258706노트

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HRID 258706 반응식
C(O[CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:27])[CH:10]2[NH:14][C:15](=[O:26])[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[S:22]([CH3:25])(=[O:24])=[O:23])[C:7]=1[C:28]([OH:30])=[O:29])(=O)C.[C:31](=O)(O)[O-].[Na+].[CH3:36][C:37]1[S:38][C:39](=[S:42])[NH:40][N:41]=1.[OH2:43]>>[CH:6]([O:43][CH:37]([CH3:36])[CH3:31])([CH3:7])[CH3:5].[C:28]([C:7]1[N:8]2[CH:11]([S:12][CH2:13][C:6]=1[CH2:5][S:42][C:39]1[S:38][C:37]([CH3:36])=[N:41][N:40]=1)[CH:10]([NH:14][C:15](=[O:26])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[S:22]([CH3:25])(=[O:23])=[O:24])[C:9]2=[O:27])([OH:30])=[O:29]

참가 물질

6

반응물 4

HCID 962Water2회HCID 516892Sodium Bicarbonate2회HCID 18102035-Methyl-1,3,4-thiadiazole-2(3H)-thioneHCID 21426436HCID 21426436, 화합물

생성물 2

HCID 7914Diisopropyl EtherHCID 21426447HCID 21426447, 화합물

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온도
60 °C

실험 절차

3-Acetoxymethyl-2-carboxy-7-[(2-mesyl-imidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (13.7 g.) and sodium bicarbonate (2.52 g.) are dissolved in water (140 cc.). A solution of 2-methyl-5-thioxo-1,3,4-thiadiazoline (4.75 g.) and sodium bicarbonate (3.0 g.) in water (160 cc.) is added. The mixture is heated at 60° C. for 12 hours. The mixture is allowed to cool, washed with ethyl acetate (100 cc.) and acidified to pH 2 by adding 6 N hydrochloric acid. A product precipitates and is filtered off and taken up, with stirring, in methanol (20 cc.). The solid is again filtered off and washed with methanol (40 cc.) and then with isopropyl ether (30 cc.) to give 2-carboxy-7-[(2-mesyl-imidazol-1-yl)-acetamido]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-8-oxo-5-thia-1-aza-bicyclo-[4,2,0]oct-2-ene (6.2 g.), m.p. approximately 196° C., [α]D20 = -56° ± 2° (c= 1, dimethylformamide).

후처리

  1. temperatureto cool
  2. washwashed with ethyl acetate (100 cc.)
  3. additionby adding 6 N hydrochloric acid
  4. customA product precipitates
  5. filtrationis filtered off
  6. filtrationThe solid is again filtered off
  7. washwashed with methanol (40 cc.)

출처 및 근거

ORD 기록
ord-dc5f410afd824d989500a40da04fc489
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04034088

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