Boric Acid → 7-Amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 1979617Notes

Reaction equation

HRID 1979617 reaction equation
[SH:1][C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.B(O)(O)O.C(N(CC)CC)C.[NH2:19][CH:20]1[C:35](=[O:36])[N:22]2[C:23]([C:32]([OH:34])=[O:33])=[C:24]([CH2:27]OC(=O)C)[CH2:25][S:26][C@H:21]12>O>[NH2:19][CH:20]1[C:35](=[O:36])[N:22]2[C:23]([C:32]([OH:34])=[O:33])=[C:24]([CH2:27][S:1][C:2]3[S:3][C:4]([CH3:7])=[N:5][N:6]=3)[CH2:25][S:26][C@H:21]12

Participants

6

Reactant 4

HCID 7628Boric AcidHCID 8471TriethylamineHCID 113463103-Acetoxymethyl-7-amino-3cephem-4-carboxylic acidHCID 178434161HCID 178434161, compound

Product 1

HCID 129420347-Amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 40 g (0.30 mole) of 2-mercapto-5-methyl-1,3,4-thiadiazole (TD) in 3.15 liters of water, with 30 g of boric acid and 30.4 ml (≃0.217 mole) of triethylamine was heated to 70/72° C. While the mixture was being vigorously stirred, at the same temperature, one 40 g shot (0.147 mole) of 7-amino-3-acetoxymethyl-3-cephem-4-carboxylic acid (92%) was added.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-9e27d12a9e3c4b2a891a89d583a4159f
Source dataset
uspto-grants-1984_11
Patent number
US04481357

Reaction notes

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