Sodium Acetate → sodium (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1934795Notes

Reaction equation

HRID 1934795 reaction equation
SC1([CH:13](Br)[C:14](=O)/[C:15](=[N:19]/[O:20][CH3:21])/[C:16]([O-:18])=O)NN=C(C2C=CC=CC=2)O1.[NH2:24][C:25]([NH2:27])=[S:26].C([O-])(=O)C.[Na+:32].[NH2:33][CH:34]1[C:55](=[O:56])[N:36]2[C:37]([C:52]([OH:54])=[O:53])=[C:38]([CH2:41][S:42][C:43]3[N:44]([CH3:51])[N:45]=[C:46]([OH:50])[C:47](=[O:49])[N:48]=3)[CH2:39][S:40][C@H:35]12>O.C(N(CC)CC)C.C1COCC1>[CH3:51][N:44]1[N:45]=[C:46]([OH:50])[C:47](=[O:49])[N:48]=[C:43]1[S:42][CH2:41][C:38]1[CH2:39][S:40][C@@H:35]2[C@H:34]([NH:33][C:16](/[C:15](/[C:14]3[N:24]=[C:25]([NH2:27])[S:26][CH:13]=3)=[N:19]\[O:20][CH3:21])=[O:18])[C:55](=[O:56])[N:36]2[C:37]=1[C:52]([O-:54])=[O:53].[Na+:32]

Participants

8

Reactant 4

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 178481957HCID 178481957, compoundHCID 178502847HCID 178502847, compound

Product 1

HCID 178502823sodium (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 170.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

2-mercapto-5-phenyl-1,3,4-oxadiazolyl-(Z)-4-bromo-2-methoxyimino-3-oxo-butyrate (27.0 g) was taken in mixture of THF (250 ml) and water (125 ml). Thiourea (10.6 g) and sodium acetate (2.0 g) were added to this at 10-15° C. after 45 to 60 min. 7-Amino-3-[[(2, 5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazin-3yl)thio]methyl]3-cephem-4-carboxylic acid (20.0 g) was suspended in the reaction mixture. The suspension was stirred for 2-3 hours at a pH of 7.0-8.5 maintained by triethylamine to get clear solution. The reaction mixture was monitored by HPLC. After completion of reaction, 200 ml water was added and pH was adjusted to 7.0. The aqueous layer was separated, charcoalized and treated with sodium-2-ethylhexanoate (30.5 g) in acetone, reaction was proceeded by same method as mentioned in Method -I to get crude ceftriaxone sodium (24.0 g).

Workup

  1. customto get clear solution
  2. additionwas added
  3. customThe aqueous layer was separated
  4. additiontreated with sodium-2-ethylhexanoate (30.5 g) in acetone, reaction

Sources & evidence

ORD record
ord-4f56bf1d29bf42bd85431807eb4f5076
Source dataset
uspto-grants-2002_05
Patent number
US06384215B1

Reaction notes

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