Phosphorus trichloride → HCID 54234928, compound

HRID 463593Notes

Reaction equation

HRID 463593 reaction equation
P(Cl)(Cl)Cl.[CH:5]([O:18][C:19]([C:21]1[N:22]2[CH:25]([S:26](=O)[CH2:27][C:28]=1[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31])[CH:24]([NH:39][C:40](=[O:70])[C:41](=[N:67][O:68][CH3:69])[C:42]1[N:43]=[C:44]([NH:47][C:48]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[S:45][CH:46]=1)[C:23]2=[O:71])=[O:20])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC(N(C)C)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH:5]([O:18][C:19]([C:21]1[N:22]2[CH:25]([S:26][CH2:27][C:28]=1[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31])[CH:24]([NH:39][C:40](=[O:70])[C:41](=[N:67][O:68][CH3:69])[C:42]1[N:43]=[C:44]([NH:47][C:48]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[S:45][CH:46]=1)[C:23]2=[O:71])=[O:20])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 24387Phosphorus trichlorideHCID 31374DimethylacetamideHCID 516892Sodium BicarbonateHCID 54105442HCID 54105442, compound

Product 1

HCID 54234928HCID 54234928, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-8 °C

Procedure

Phosphorus trichloride (0.81 cc) is added, in the course of 1 minute, to a solution of the syn isomer of 2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-3-phenacyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (4.3 g) and dimethylacetamide (1.88 cc) in methylene chloride (43 cc), cooled to -8° C., and the mixture is left for 1 hour at -8° C., whilst stirring. The mixture is then poured into a saturated solution of sodium bicarbonate (20 cc) and ethyl acetate (100 cc). The organic phase is washed with water (30 cc), dried over magnesium sulphate and evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. The residue is dissolved in ethyl acetate (15 cc) and the solution is filtered on Merck silica gel (0.06-0.2) (13 g) and washed through with ethyl acetate (20 cc). The filtrate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. This yields the syn isomer of 2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-3-phenacyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene (3.6 g) in the form of a beige solid.

Workup

  1. washThe organic phase is washed with water (30 cc)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C
  4. dissolutionThe residue is dissolved in ethyl acetate (15 cc)
  5. filtrationthe solution is filtered on Merck silica gel (0.06-0.2) (13 g)
  6. washwashed through with ethyl acetate (20 cc)
  7. customThe filtrate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C

Sources & evidence

ORD record
ord-5c4b49033ab844aea718bfc63b361ddb
Source dataset
uspto-grants-1985_05
Patent number
US04520193

Reaction notes

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