Phosphorus trichloride → 3-Acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 463587Notes

Reaction equation

HRID 463587 reaction equation
[CH2:1]([C:5]1[CH2:12][S:11](=O)[CH:10]2[N:7]([C:8](=[O:46])[CH:9]2[NH:14][C:15](=[O:45])[C:16](=[N:42][O:43][CH3:44])[C:17]2[N:18]=[C:19]([NH:22][C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:20][CH:21]=2)[C:6]=1[C:47]([O:49][CH:50]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48])[C:2]([CH3:4])=[O:3].P(Cl)(Cl)Cl>C(Cl)Cl.CN(C)C(=O)C.C(OCC)(=O)C>[CH2:1]([C:5]1[CH2:12][S:11][CH:10]2[N:7]([C:8](=[O:46])[CH:9]2[NH:14][C:15](=[O:45])[C:16](=[N:42][O:43][CH3:44])[C:17]2[N:18]=[C:19]([NH:22][C:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[S:20][CH:21]=2)[C:6]=1[C:47]([O:49][CH:50]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:48])[C:2]([CH3:4])=[O:3]

Participants

6

Reactant 2

HCID 24387Phosphorus trichlorideHCID 537724793-Acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide

Product 1

HCID 544195633-Acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-eneYield 91.7%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 3-acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (5 g) in a mixture of methylene chloride (60 cc) and N,N-dimethylacetamide (2.3 cc) is cooled to -10° C. Phosphorus trichloride (1.01 cc) is then added and the mixture is stirred for one hour at -10° C. The reaction mixture is diluted with ethyl acetate (300 cc), washed successively with a saturated solution of sodium bicarbonate (50 cc) and distilled water (300 cc), dried over sodium sulphate and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. This yields the syn isomer of 3-acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (4.5 g) in the form of a hard yellow foam.

Workup

  1. washwashed successively with a saturated solution of sodium bicarbonate (50 cc)
  2. distillationdistilled water (300 cc)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C

Sources & evidence

ORD record
ord-0b3607e9ad5244f68792d9835225073a
Source dataset
uspto-grants-1985_05
Patent number
US04520193

Reaction notes

Loading…