Dimethylformamide → HCID 131717474, compound

HRID 655055Notes

Reaction equation

HRID 655055 reaction equation
CN(C)C=O.[C:6](Cl)(=[O:10])[C:7](Cl)=O.[C:12]([O:16][C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25](=[N:29][O:30][C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]([OH:28])=O)[N:24]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[CH3:50]N1CCOCC1.[C:57]1([CH3:67])[CH:62]=CC(S(O)(=O)=O)=[CH:59][CH:58]=1.[NH2:68][C@@H:69]1[C:81](=[O:82])[N:71]2[C:72]([C:78]([OH:80])=[O:79])=[C:73]([CH2:76][Cl:77])[CH2:74][S:75][C@H:70]12>ClCCl>[CH3:50][O:10][C:6]1[CH:7]=[CH:62][C:57]([CH2:67][O:79][C:78]([C:72]2[N:71]3[C:81](=[O:82])[C@@H:69]([NH:68][C:26](=[O:28])[C:25]([C:23]4[N:24]=[C:20]([NH:19][C:17]([O:16][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:18])[S:21][CH:22]=4)=[N:29][O:30][C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C@H:70]3[S:75][CH2:74][C:73]=2[CH2:76][Cl:77])=[O:80])=[CH:58][CH:59]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 79724-Methylmorpholine2×HCID 65578Oxalyl chlorideHCID 54559146HCID 54559146, compoundHCID 88394649HCID 88394649, compound

Product 1

HCID 131717474HCID 131717474, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,N-dimethylformamide (0.321 ml; 1 Eq.) in dichloromethane (20 ml) keeping at -10° C. is added dropwise oxalyl chloride (0.354 ml; 1.64 Eq.), and the mixture is stirred at -10° to -5° C. for 15 minutes. To this mixture are added a solution of 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-triphenylmethoxyiminoacetic acid (2.0 g; 09 Eq.) in dichloromethane (10 ml) and N-methylmorpholine (0.502 ml; 1.1 Eq.), and the mixture is stirred at -10° to -5° C. for 30 minutes. To this solution is added a solution of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-toluenesulfonate (2.4 g; 4.16 mMol.). To this mixture is added N-methylmorpholine (0.502 ml; 1 Eq.), and the mixture is stirred at -10° to -5° C. for 45 minutes. The reaction mixture is diluted with ice water and extracted with dichloromethane. The extract is washed with hydrochloric acid, aqueous sodium hydrogen carbonate, and water, dried, and concentrated in vacuum. The residue is purified by silica gel chromatography (toluene:ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-trityloxyimino-acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (2.38 g).

Workup

  1. customkeeping at -10° C.
  2. stirringthe mixture is stirred at -10° to -5° C. for 30 minutes
  3. stirringthe mixture is stirred at -10° to -5° C. for 45 minutes
  4. extractionextracted with dichloromethane
  5. washThe extract is washed with hydrochloric acid, aqueous sodium hydrogen carbonate, and water
  6. customdried
  7. concentrationconcentrated in vacuum
  8. customThe residue is purified by silica gel chromatography (toluene:ethyl acetate)

Sources & evidence

ORD record
ord-0ed418b3d25f4f8ca0be73e3cc986584
Source dataset
uspto-grants-1992_07
Patent number
US05134138

Reaction notes

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