Trimethyl borate → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

HRID 1087254Notes

Reaction equation

HRID 1087254 reaction equation
C[C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[Sb](Cl)(Cl)(Cl)(Cl)Cl.[Bi](Cl)(Cl)Cl.B(OC)(OC)OC>S1(CCCC1)(=O)=O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][O:4][CH3:2])[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 4

HCID 8470Trimethyl borateHCID 24294Antimony pentachlorideHCID 24591Bismuth trichlorideHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
50 °C

Procedure

To 10 ml of sulfolane were added 1.41 g of 7-ACA, 0.60 ml of antimony pentachloride, 15.18 g of bismuth trichloride and 1.95 ml of trimethyl borate. The mixture was heated at 50° C. for 5 hours to advance a reaction. After completion of the reaction, substantially the same procedure as in Example 1 was repeated, to thereby obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 0.81 g. The yield of the desired product was 64%.

Workup

  1. customa reaction
  2. customAfter completion of the reaction

Sources & evidence

ORD record
ord-d6631d6663c742e782daa6560228918b
Source dataset
uspto-grants-1991_07
Patent number
US05034521

Reaction notes

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