Hydrochloric Acid → HCID 131716051, compound

HRID 1074352Notes

Reaction equation

HRID 1074352 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:46]2[N:47]=[C:48]([NH:51]C=O)[S:49][CH:50]=2)[C:7]([NH:9][C@@H:10]2[C:44](=[O:45])[N:12]3[C:13]([C:28]([O:30][CH:31]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[O:29])=[C:14]([CH2:17][S:18][C:19]4[N:24]([CH3:25])[C:23](=[O:26])[C:22](=[O:27])[NH:21][N:20]=4)[CH2:15][S:16][C@H:11]23)=[O:8])[CH2:3][CH2:2]1.Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[NH2:51][C:48]1[S:49][CH:50]=[C:46]([C:6](=[N:5][O:4][CH:1]2[CH2:2][CH2:3]2)[C:7]([NH:9][C@@H:10]2[C:44](=[O:45])[N:12]3[C:13]([C:28]([O:30][CH:31]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:29])=[C:14]([CH2:17][S:18][C:19]4[N:24]([CH3:25])[C:23](=[O:26])[C:22](=[O:27])[NH:21][N:20]=4)[CH2:15][S:16][C@H:11]23)=[O:8])[N:47]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 131716052HCID 131716052, compound

Product 1

HCID 131716051HCID 131716051, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a suspension of benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(5,6-dioxo-4-methyl-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (1.10 g) in a mixture of methanol (7.5 ml) and tetrahydrofuran (4 ml) was added concentrated hydrochloric acid (0.44 ml) and the mixture was stirred at 35° C. for an hour. The mixture was poured into a mixture of ethyl acetate (100 ml) and ice-water (100 ml) and adjusted to pH 7 with saturated aqueous solution of sodium bicarbonate. The organic layer was separated, washed with saturated aqueous solution of sodium chloride and water successively and concentrated in vacuo. The residue was subjected to column chromatography on silica gel (30 g) using a mixture of chloroform and methanol (30:1 V/V) as an eluent to give benzhydryl 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-(5,6-dioxo-4-methyl-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (356 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous solution of sodium chloride and water successively
  3. concentrationconcentrated in vacuo
  4. additiona mixture of chloroform and methanol (30:1 V/V) as an eluent

Sources & evidence

ORD record
ord-d09a5f5232e244429c2fded49cb3e93c
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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