Triethylsilane → Ceftobiprole Medocaril Sodium

HRID 1633815Notes

Reaction equation

HRID 1633815 reaction equation
C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH:25]=[C:26]1[CH2:30][CH2:29][N:28]([CH:31]3[CH2:35][CH2:34][N:33]([C:36]([O:38][CH2:39][C:40]4[O:41][C:42](=[O:46])[O:43][C:44]=4[CH3:45])=[O:37])[CH2:32]3)[C:27]1=[O:47])[CH:20]([NH:48][C:49](=[O:78])[C:50]([C:72]1[N:76]=[C:75]([NH2:77])[S:74][N:73]=1)=[N:51][O:52]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:19]2=[O:79])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[NH2:77][C:75]1[S:74][N:73]=[C:72](/[C:50](=[N:51]/[OH:52])/[C:49]([NH:48][C@@H:20]2[C:19](=[O:79])[N:18]3[C@@H:21]2[S:22][CH2:23][C:24](/[CH:25]=[C:26]2/[C:27](=[O:47])[N:28]([C@@H:31]4[CH2:35][CH2:34][N:33]([C:36]([O:38][CH2:39][C:40]5[O:41][C:42](=[O:46])[O:43][C:44]=5[CH3:45])=[O:37])[CH2:32]4)[CH2:29][CH2:30]/2)=[C:17]3[C:15]([OH:16])=[O:14])=[O:78])[N:76]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 865843727-[2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyimino-acetylamino]-3-[1'-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethoxycarbonyl)-2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Product 1

HCID 135413544Ceftobiprole Medocaril SodiumYield 91.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 40 mg 7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyimino-acetylamino]-3-[1′-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethoxycarbonyl)-2-oxo-[1,3′]bipyrrolidinyl-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester and 20 mg triethylsilane is dissolved in 0.30 ml trifluoroacetic acid. The resulting solution is stirred at 0° C. for 15 min. The solvent is evaporated under aspirator vacuum and the residue is triturated with diethyl ether. The solid is collected by filtration and washed with diethyl ether to yield 23 mg of the title compound as beige powder. MS: M−H=689.3. 1H-NMR (d6-DMSO): 13.8 (s, 1H, COOH); 11.9 (s, 1H, OH); 9.45 (d, J=8.4, 1H, NH); 8.05 (s, 2H, NH2); 7.31(s, 1H, HC═C); 5.86 (dd, J=8.4; 4.8, 1H CH); 5.17 (d, J=8.4, 1H CH); 4.61 (m, 1H CH); 3.85 (m, 2H CH2); 3.55-3.35 (m, 6H 3×CH2); 3.1 (m, 1H); 2.9 (m, 1H); 2.15 (s, 3H, CH3); 2.05 (m, 2H CH2).

Workup

  1. customThe solvent is evaporated under aspirator vacuum
  2. customthe residue is triturated with diethyl ether
  3. filtrationThe solid is collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c46f20b96fa349d09348e7e9b0a1e257
Source dataset
uspto-grants-2003_01
Patent number
US06504025B2

Reaction notes

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