1,1-Dimethyl-2-thiourea → 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 2413421Notes

Reaction equation

HRID 2413421 reaction equation
[CH3:1][N:2]([CH3:6])[C:3]([NH2:5])=[S:4].[CH:7]([O:20][C:21]([C:23]1[N:24]2[CH:27]([S:28][CH2:29][C:30]=1[CH:31]=[CH:32]N(C)C)[CH:26]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:25]2=[O:44])=[O:22])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH:7]([O:20][C:21]([C:23]1[N:24]2[CH:27]([S:28][CH2:29][C:30]=1[C:31]1[S:4][C:3]([N:2]([CH3:6])[CH3:1])=[N:5][CH:32]=1)[CH:26]([NH:36][C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[C:25]2=[O:44])=[O:22])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 30341921,1-Dimethyl-2-thioureaHCID 539143342-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylamino-vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 204304082-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-eneYield 58.3%

Procedure

The working method of Example 2 is followed, but replacing the thiourea by N,N-dimethylthiourea (5.25 g) and starting with 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylamino-vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (E-form) (21.4 g). The product obtained is chromatographed on a column (diameter: 4.5 cm) containing silica gel (0.2-0.06 mm)(500 cc), elution being carried out with methylene chloride (5 liters) and then with mixtures of methylene chloride and ethyl acetate, namely 99:1 by volume (5 liters) followed by 97:3 by volume (7.5 liters), and 500 cc fractions being collected; fractions 13 to 34 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. The residue is triturated with isopropyl ether (100 cc) and 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (13.8 g) is obtained in the form of a yellow solid.

Workup

  1. customThe product obtained
  2. customis chromatographed on a column (diameter: 4.5 cm)
  3. additioncontaining
  4. washsilica gel (0.2-0.06 mm)(500 cc), elution
  5. custombeing collected
  6. concentrationfractions 13 to 34 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C
  7. customThe residue is triturated with isopropyl ether (100 cc)

Sources & evidence

ORD record
ord-329a48697ef240f89471820a6692048b
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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