Methane → 7-Phenylacetamido-3-formyl-3-cephem-4-carboxylic acid benzhydrylester

HRID 1108008

Reaction equation

HRID 1108008 reaction equation
[NH2:1][CH:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([OH:13])=[O:12])=[C:6]([CH:9]=[O:10])[CH2:7][S:8][C@H:3]12.[CH3:16][C:17]([O:23][Si](C)(C)C)=N[Si](C)(C)C.[C:28]1([CH2:34][C:35](Cl)=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH4:38].[CH3:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>O>[CH:34]([O:12][C:11]([C:5]1[N:4]2[C:14](=[O:15])[CH:2]([NH:1][C:17](=[O:23])[CH2:16][C:41]3[CH:40]=[CH:39][CH:44]=[CH:43][CH:42]=3)[C@H:3]2[S:8][CH2:7][C:6]=1[CH:9]=[O:10])=[O:13])([C:35]1[CH:7]=[CH:6][CH:5]=[CH:11][CH:38]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 5

HCID 297MethaneHCID 7679Phenylacetyl chlorideHCID 8058HexaneHCID 25248trimethylsilyl N-trimethylsilylethanimidateHCID 872037627-Amino-3-formyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317210617-Phenylacetamido-3-formyl-3-cephem-4-carboxylic acid benzhydrylester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.28 g of 7-amino-3-formyl-3-cephem-4-carboxylic acid are bisilylated as described in example 19 with 5.4 ml of N,O-bis-(trimethylsilyl)-acetamide, reacted with phenylacetic acid chloride, and then hydrolysed with 0.4 ml of water. The hydrolysed reaction mixture is treated with 1 g of activated charcoal and then filtered. The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane, and then concentrated to 10 ml in vacuo. The product is precipitated from the residue of evaporation thus obtained by adding 100 ml of n-hexane. 7-phenylactamido-3-formyl-3-cephem-4-carboxylic acid benzhydrylester is thus obtained as a slightly yellowish product. 1H-NMR (60 MHz, d6 -DMSO): 3.15 (ABq, J=18 Hz, 2H, SCH2); 3.55 (s, 2H, --CH2 --CO); 4.9 (d, J=5 Hz, 1H, H-6); 5.90 (dd, J=5 and 8 Hz, 1H, H-7); 6.6 (d, J=8 Hz, 1H, NH); 7.0 (s, 1H, CHPh2); 7.25 and 7.30 (2s, 15H, Ar--H); 9.62 (s, 1H, CH=O).

Workup

  1. filtrationfiltered
  2. additionThe yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane
  3. concentrationconcentrated to 10 ml in vacuo
  4. customThe product is precipitated from the residue of evaporation
  5. customthus obtained

Sources & evidence

ORD record
ord-b96d06f4dcb941a3b3e258141ecc29ae
Source dataset
uspto-grants-2000_05
Patent number
US06063917

Linked notes

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