Chloroform → HCID 15378845, compound

HRID 2209832Notes

Reaction equation

HRID 2209832 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[C:15](OS(C(F)(F)F)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Sn](C)(C)[C:46]1[CH:47]=[CH:48][C:49]2[C:50](=[O:61])[C:51]3[C:56]([C:57]=2[CH:58]=1)=[CH:55][CH:54]=[C:53]([CH2:59][OH:60])[CH:52]=3.C(Cl)(Cl)Cl>CN1CCCC1=O.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28][CH:29]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[O:27])=[C:15]([C:46]4[CH:47]=[CH:48][C:49]5[C:50](=[O:61])[C:51]6[C:56]([C:57]=5[CH:58]=4)=[CH:55][CH:54]=[C:53]([CH2:59][OH:60])[CH:52]=6)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 3

HCID 6212ChloroformHCID 11072274HCID 11072274, compoundHCID 15661375HCID 15661375, compound

Product 1

HCID 15378845HCID 15378845, compoundYield 61.2%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Benzhydryl 7β-phenylacetamido-3-trifluormethanesulfonyloxy-ceph-3-em-4-carboxylate (1.26 g) was dissolved in N-methylpyrrolidone (NMP) and treated with 3-trimethylstannyl-7-hydroxymethyl-9-fluorenone (0.742 g). Zinc chloride (4.0 ml, 1.0M solution in ether) was added followed by Pd2 (dba)3.CHCl3 (60 mg) and the reaction mixture was stirred under nitrogen for 45 min. The reaction mixture was diluted with ethyl acetate and washed with water five times, then with saturated sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was crystallized from hot ethyl acetate/hexane to give 0.844 g of the desired product in the first crop and a further 0.170 g in the second crop of crystals.

Workup

  1. washwashed with water five times
  2. dry with materialwith saturated sodium chloride solution and then dried over anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was crystallized from hot ethyl acetate/hexane

Sources & evidence

ORD record
ord-c7f7d8ddd6fd482287e09417a9d01d92
Source dataset
uspto-grants-1995_10
Patent number
US05455239

Reaction notes

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