Water → HCID 54274141, compound

HRID 905386Notes

Reaction equation

HRID 905386 reaction equation
C(O[CH:6](N(C)C)[N:7]([CH3:9])[CH3:8])(C)(C)C.[CH:13]([O:26][C:27]([C:29]1[N:30]2[CH:33]([S:34][CH2:35][C:36]=1[CH3:37])[CH:32]([NH:38][C:39](=[O:78])[C:40](=[N:66][O:67][C:68]([C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])([CH3:70])[CH3:69])[C:41]1[N:42]=[C:43]([NH:46][C:47]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[S:44][CH:45]=1)[C:31]2=[O:79])=[O:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C.O>CN(C)C=O>[CH:13]([O:26][C:27]([C:29]1[N:30]2[CH:33]([S:34][CH2:35][C:36]=1[CH:37]=[CH:6][N:7]([CH3:9])[CH3:8])[CH:32]([NH:38][C:39](=[O:78])[C:40](=[N:66][O:67][C:68]([C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])([CH3:70])[CH3:69])[C:41]1[N:42]=[C:43]([NH:46][C:47]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)([C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[S:44][CH:45]=1)[C:31]2=[O:79])=[O:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 54102918HCID 54102918, compound

Product 1

HCID 54274141HCID 54274141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butoxy-bis dimethylaminomethane (1.9 cc) is added, whilst stirring, to a solution, at 80° C., under nitrogen, of the syn isomer of 2-benzhydryloxycarbonyl-7-{2-[(2-t-butoxycarbonylprop-2-yl)-oxyimino]-2-(2-tritylaminothiazol-4-yl)-acetamido}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (6 g.) in dimethylformamide (64 cc), and the reaction is continued for 15 minutes. The mixture is then poured into a mixture of ethyl acetate (200 cc) and water (200 cc). The organic phase is decanted, washed with water (3×100 cc) and a saturated aqueous solution of sodium chloride (100 cc), dried over sodium sulphate and filtered and the filtrate is concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). This yields crude E form of the syn isomer of 2-benzhydryloxycarbonyl-3-(2-dimethylaminovinyl)-7-{2-(2-t-butoxycarbonylprop-2-yl-oxyimino)-2-(2-tritylaminothiazol-4-yl)-acetamido}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct- 2-ene (6.5 g) in the form of a hard brown foam.

Workup

  1. customThe organic phase is decanted
  2. washwashed with water (3×100 cc)
  3. dry with materiala saturated aqueous solution of sodium chloride (100 cc), dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)

Sources & evidence

ORD record
ord-0d3c742008da4d52a2abc881b3fd54b7
Source dataset
uspto-grants-1983_12
Patent number
US04423214

Reaction notes

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