Sodium Bicarbonate → 7-(Thien-3-ylacetamido)-3-(1-carbamoylmethyl-1H-tetrazol-5-ylthio)-methylceph-3-em-4-carboxylic acid

HRID 2049569Notes

Reaction equation

HRID 2049569 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([NH:9][CH:10]2[C:25](=[O:26])[N:12]3[C:13]([C:22]([O-:24])=[O:23])=[C:14](COC(=O)C)[CH2:15][S:16][C@H:11]23)=[O:8])=[CH:2]1.[Na+].[SH:28][C:29]1[N:33]([CH2:34][C:35]([NH2:37])=[O:36])[N:32]=[N:31][N:30]=1.[C:38](=O)(O)[O-].[Na+].[Na]>P([O-])([O-])([O-])=O.CC(C)=O.CC(C)CC(=O)C.CCOCC>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([NH:9][CH:10]2[C:25](=[O:26])[N:12]3[C:13]([C:22]([OH:24])=[O:23])=[C:14]([S:28][C:29]4[N:33]([CH2:34][C:35](=[O:36])[NH2:37])[N:32]=[N:31][N:30]=4)[CH:15]([CH3:38])[S:16][C@H:11]23)=[O:8])=[CH:2]1

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 70591295Sodium 7-(thien-3-ylacetamido)-3-acetoxymethylceph-3-em-4-carboxylateHCID 178514025HCID 178514025, compound

Product 1

HCID 1317117437-(Thien-3-ylacetamido)-3-(1-carbamoylmethyl-1H-tetrazol-5-ylthio)-methylceph-3-em-4-carboxylic acidYield 42.1%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 1061PhosphateSolventHCID 3283Diethyl EtherSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

Sodium 7-(thien-3-ylacetamido)-3-acetoxymethylceph-3-em-4-carboxylate (1.90 g, 4.6 mmole), 5-mercapto-1H-tetrazol-1-ylacetamide (0.81 g, 5.1 mmole) and sodium bicarbonate (0.42 g, 5 mmole) in pH 6.5 phosphate buffer (25 ml) were heated at 60° for 6 hours, then poured onto ice, washed with ethyl acetate (25 ml), acidified to pH 1.5 and extracted with ethyl acetate (3×20 ml). The extracts were washed with water and saturated brine, dried, evaporated to dryness and the residue triturated with anhydrous ether to give the free acid, 1.59 g. This was dissolved in acetone (25 ml), treated with 2 N sodium 2-ethylhexoate in 4-methylpentan-2-one (1.5 ml), diluted with anhydrous ether (25 ml) and the precipitated sodium salt collected, washed with ether and dried, 1.00 g, 42.1% yield; t.l.c. (SiO2 ; B.A.W; 12:3:5) Rf=0.40; λmax (95% ethanol) 273 nm (ε=8,200); δ[(CD3)2SO] 3.2-3.7 (2H,m, C2 methylene), 3.38 (2H,s, --CH2CONH--), 4.04-4.25 (2H, ABq, J 13 Hz, --CH2S--), 4.73 (1H,d, J 5 Hz, C6 proton), 4.87 (2H,s, --CH2CONH2), 5.50 (1H,dd, J 5 and 8 Hz, C7 proton), 6.9-8.2 (5H,m, thienyl protons and --CONH2), 8.88 (1H,d, J 8 Hz, --CONH--).

Workup

  1. additionpoured onto ice
  2. washwashed with ethyl acetate (25 ml)
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. washThe extracts were washed with water and saturated brine
  5. customdried
  6. customevaporated to dryness
  7. customthe residue triturated with anhydrous ether
  8. customto give the free acid, 1.59 g
  9. customthe precipitated sodium salt collected
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-d0db71bce01b4c6da30049f431f75d99
Source dataset
uspto-grants-1980_04
Patent number
US04198406

Reaction notes

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