Phosphorus pentachloride → HCID 13239638, compound

HRID 1995936Notes

Reaction equation

HRID 1995936 reaction equation
[NH2:1][CH:2]1[C:27](=[O:28])[N:4]2[C:5]([C:11]([O:13][CH:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])=[C:6]([CH2:9][Cl:10])[CH2:7][S:8][C@H:3]12.[CH2:29]([O:32]/[N:33]=[C:34](/[C:38]1[N:39]=[C:40]([NH:43][C:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[S:41][CH:42]=1)\[C:35](O)=[O:36])[CH:30]=[CH2:31].P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl.C(OCC)(=O)C>[CH2:29]([O:32]/[N:33]=[C:34](/[C:38]1[N:39]=[C:40]([NH:43][C:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[S:41][CH:42]=1)\[C:35]([NH:1][CH:2]1[C:27](=[O:28])[N:4]2[C:5]([C:11]([O:13][CH:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:12])=[C:6]([CH2:9][Cl:10])[CH2:7][S:8][C@H:3]12)=[O:36])[CH:30]=[CH2:31]

Participants

6

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 12784196HCID 12784196, compoundHCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylate2×

Product 1

HCID 13239638HCID 13239638, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of Compound V (1.35 g, 3 mmoles) in methylene chloride (20 mL) was added BSA (1.1 mL, 4.5 mmoles), and the mixture was stirred for 30 minutes at room temperature to become a clear solution. A mixture of (Z)-2-allyloxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid (IVd) (1.40 g, 3.0 mmoles) and phosphorus pentachloride (690 mg, 3.3 mmoles) in methylene chloride (20 mL) was stirred for 15 minutes at room temperature and poured in one portion into the solution of the trimethylsilylated Compound V. The mixture was stirred for 20 minutes at room temperature and diluted with ethyl acetate (200 mL), washed with aqueous sodium bicarbonate and water, dried and evaporated under reduced pressure. The oily residue was purified by silica gel column chromatography (Wako-gel, C-200, 30 g). The column was eluted with chloroform and the fractions containing the desired product were combined. Evaporation under reduced pressure afforded the title compound (VId) as an amorphous powder, yield 2.32 g (89%). Mp. 100-115° C. (dec.).

Workup

  1. additionwas added BSA (1.1 mL, 4.5 mmoles)
  2. stirringwas stirred for 15 minutes at room temperature
  3. stirringThe mixture was stirred for 20 minutes at room temperature
  4. washwashed with aqueous sodium bicarbonate and water
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe oily residue was purified by silica gel column chromatography (Wako-gel, C-200, 30 g)
  8. washThe column was eluted with chloroform
  9. additionthe fractions containing the desired product
  10. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-c0a1d125a60c4a368f62f6badd935105
Source dataset
uspto-grants-1983_09
Patent number
US04406899

Reaction notes

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