Sodium Bicarbonate → benzhydryl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 247753Notes

Reaction equation

HRID 247753 reaction equation
Cl.[NH2:2][CH:3]1[C:30](=[O:31])[N:5]2[C:6]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:7](/[CH:10]=[CH:11]\[CH2:12][CH3:13])[CH2:8][S:9][C@H:4]12.C([O-])(O)=O.[Na+].[NH2:37][C:38]1[S:39][CH:40]=[C:41](/[C:43](=[N:56]/[O:57][CH3:58])/[C:44](ON2C3C=CC=CC=3N=N2)=[O:45])[N:42]=1>C(OCC)(=O)C>[NH2:37][C:38]1[S:39][CH:40]=[C:41](/[C:43](=[N:56]/[O:57][CH3:58])/[C:44]([NH:2][CH:3]2[C:30](=[O:31])[N:5]3[C:6]([C:14]([O:16][CH:17]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:15])=[C:7](/[CH:10]=[CH:11]\[CH2:12][CH3:13])[CH2:8][S:9][C@H:4]23)=[O:45])[N:42]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 102453094-{(1Z)-2-[(1H-Benzotriazol-1-yl)oxy]-N-methoxy-2-oxoethanimidoyl}-1,3-thiazol-2-amineHCID 70445679diphenylmethyl 7-amino-3-[(Z)-1-butenyl]-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 88669278benzhydryl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of diphenylmethyl 7-amino-3-[(Z)-1-butenyl]-3-cephem-4-carboxylate hydrochloride (1.41 g, 3.1 mmoles) in ethyl acetate (20 ml) was shaken with aqueous NaHCO3 to give a clear two-layer solution. The organic layer was separated, washed with water and then an aqueous saturated NaCl solution, and dried over MgSO4. To the dried filtrate was added 1-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetoxy]benzotriazole (1.27 g, 4.0 mmoles), and the mixture was stirred at room temperature for 20 hours. The reaction mixture was filtered and the filtrate was washed with aqueous NaHCO3, water and a saturated NaCl solution, dried over MgSO4 and evaporated in vacuo. The residue was chromatographed on a silica gel column (40 g) with 3:1 CHCl3 -ethyl acetate to yield 1.7 g (91%) of the title compound. TLC (silica gel): Rf 0.25 (1:1 CHCl3 -ethyl acetate).

Workup

  1. customto give a clear two-layer solution
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialan aqueous saturated NaCl solution, and dried over MgSO4
  5. filtrationThe reaction mixture was filtered
  6. washthe filtrate was washed with aqueous NaHCO3, water
  7. dry with materiala saturated NaCl solution, dried over MgSO4
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on a silica gel column (40 g) with 3:1 CHCl3 -ethyl acetate

Sources & evidence

ORD record
ord-846f15475dc248dda24962435a57061a
Source dataset
uspto-grants-1987_11
Patent number
US04708955

Reaction notes

Loading…