Hydrochloric Acid → HCID 131713092, compound

HRID 1284658Notes

Reaction equation

HRID 1284658 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:43]1[N:44]=[C:45]([NH:48]C=O)[S:46][CH:47]=1)[C:5]([NH:7][CH:8]1[C:41](=[O:42])[N:10]2[C:11]([C:25]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[C:12]([CH2:15][S:16][C:17]3[N:18]=[N:19][N:20]([CH2:22][C:23]#[CH:24])[N:21]=3)[CH2:13][S:14][C@H:9]12)=[O:6].Cl.O1CCCC1>CO>[CH3:1][O:2][N:3]=[C:4]([C:43]1[N:44]=[C:45]([NH2:48])[S:46][CH:47]=1)[C:5]([NH:7][CH:8]1[C:41](=[O:42])[N:10]2[C:11]([C:25]([O:27][CH:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:26])=[C:12]([CH2:15][S:16][C:17]3[N:18]=[N:19][N:20]([CH2:22][C:23]#[CH:24])[N:21]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 131714502HCID 131714502, compound

Product 1

HCID 131713092HCID 131713092, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate (syn isomer) (2.7 g) in methanol (19.0 ml) were added conc. hydrochloric acid (0.75 g) and tetrahydrofuran (10 ml) and the mixture was stirred for 3 hours at room temperature. After the evaporation of the reaction mixture, to the residue were added water and ethyl acetate and then the resulting mixture was adjusted to pH 7.0 with a saturated aqueous solution of sodium carbonate. After the addition of tetrahydrofuran to the resulting mixture, the organic layer was separated, washed with a saturated aqueous solution of sodium chloride (×2), dried over magnesium sulfate and then evaporated. The residue was pulverized in isopropyl ether, collected by filtration, washed with isopropyl ether and then dried to give benzhydryl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(2-propynyl)-2H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylate (syn isomer) (2.0 g).

Workup

  1. customAfter the evaporation of the reaction mixture
  2. additionto the residue were added water and ethyl acetate
  3. additionAfter the addition of tetrahydrofuran to the resulting mixture
  4. customthe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride (×2)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. filtrationcollected by filtration
  9. washwashed with isopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-b0aad1897624441e99cb7cb84f89bf5b
Source dataset
uspto-grants-1986_01
Patent number
US04563450

Reaction notes

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