Formic Acid → sodium (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-[(Z)-2-(4-methylthiadiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1461172Notes

Reaction equation

HRID 1461172 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:63]/[O:64]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:27]([NH:29][CH:30]2[C:61](=[O:62])[N:32]3[C:33]([C:45]([O:47]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:46])=[C:34](/[CH:37]=[CH:38]\[C:39]4[S:43][N:42]=[N:41][C:40]=4[CH3:44])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)=O.Cl.C(=O)(O)[O-].[Na+:92]>>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:63]/[OH:64])/[C:27]([NH:29][CH:30]2[C:61](=[O:62])[N:32]3[C:33]([C:45]([O-:47])=[O:46])=[C:34](/[CH:37]=[CH:38]\[C:39]4[S:43][N:42]=[N:41][C:40]=4[CH3:44])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1.[Na+:92]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 88523270benzhydryl (6R)-3-[(Z)-2-(4-methylthiadiazol-5-yl)ethenyl]-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 23710094sodium (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-[(Z)-2-(4-methylthiadiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Procedure

Benzhydryl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate (1.38 g, 1.2 mmol) was stirred at room temperature for 1 hour by addition of formic acid (14 ml). Concentrated hydrochloric acid (0.11 ml) was added to the reaction solution and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure and the residue was cleansed with ether thereby a yellow powder product was obtained. This one was dissolved in aqueous sodium bicarbonate solution and purified by HP-20 column chromatography thereby sodium 7-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate (79 mg) was obtained.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customa yellow powder product was obtained
  3. custompurified by HP-20 column chromatography

Sources & evidence

ORD record
ord-35d23c2021db4ca6ab303298c3056906
Source dataset
uspto-grants-1991_12
Patent number
US05073551

Reaction notes

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