Water → Diisopropyl Ether

HRID 258706Notes

Reaction equation

HRID 258706 reaction equation
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]

Participants

6

Reactant 4

HCID 962Water2×HCID 516892Sodium Bicarbonate2×HCID 18102035-Methyl-1,3,4-thiadiazole-2(3H)-thioneHCID 21426436HCID 21426436, compound

Product 2

HCID 7914Diisopropyl EtherHCID 21426447HCID 21426447, compound

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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.)

Sources & evidence

ORD record
ord-dc5f410afd824d989500a40da04fc489
Source dataset
uspto-grants-1977_07
Patent number
US04034088

Reaction notes

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