Hydrochloric Acid → benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-cyclopent-2-en-1-yloxyiminoacetyl]amino]-8-oxo-3-(1H-pyrazol-4-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 619236Notes

Reaction equation

HRID 619236 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7]C=O)=[N:4][C:3]=1/[C:10](=[N:65]/[O:66][CH:67]1[CH2:71][CH2:70][CH:69]=[CH:68]1)/[C:11]([NH:13][C@@H:14]1[C:63](=[O:64])[N:16]2[C:17]([C:47]([O:49][CH:50]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[O:48])=[C:18]([S:21][CH2:22][C:23]3[CH:24]=[N:25][N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:27]=3)[CH2:19][S:20][C@H:15]12)=[O:12].CO.Cl>O1CCCC1>[NH2:7][C:5]1[S:6][C:2]([Cl:1])=[C:3](/[C:10](=[N:65]/[O:66][CH:67]2[CH2:71][CH2:70][CH:69]=[CH:68]2)/[C:11]([NH:13][C@@H:14]2[C:63](=[O:64])[N:16]3[C:17]([C:47]([O:49][CH:50]([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[O:48])=[C:18]([S:21][CH2:22][C:23]4[CH:27]=[N:26][NH:25][CH:24]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 88199050benzhydryl (6R,7R)-7-[[(2Z)-2-(5-chloro-2-formamido-1,3-thiazol-4-yl)-2-cyclopent-2-en-1-yloxyiminoacetyl]amino]-8-oxo-3-[(1-tritylpyrazol-4-yl)methylsulfanyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 88198442benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-cyclopent-2-en-1-yloxyiminoacetyl]amino]-8-oxo-3-(1H-pyrazol-4-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of solution of diphenylmethyl 7β-[2-(5-chloro-2-formylaminothiazol-4-yl)-2-(Z)-(2-cyclopenten-1-yloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (3.82 g) in the mixture of methanol (40 ml) and tetrahydrofurane (12 ml) was added dropwise conc. hydrochloric acid (i.56 ml) at room temperature. After the mixture was stirred for 3 hours, the solvent was evaporated in vacuo. The residue was diluted with the mixture of water and ethyl acetate while the pH was adjusted between 8.0 and 8.5 with saturated sodium hydrogen carbonate. The organic layer was collected, washed with water and brine and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified on silica gel (eluent: dichloromethane-acetone) to afford diphenylmethyl 7β-[2-(2-amino-5-chlorothiazol-4-yl)-2-(Z)-(2-cyclopenten-1-yloxyimino)acetamido]-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (1.77 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionThe residue was diluted with the mixture of water and ethyl acetate while the pH
  3. customThe organic layer was collected
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was purified on silica gel (eluent: dichloromethane-acetone)

Sources & evidence

ORD record
ord-f3ed72e23b3f4dd19f034a258e83a0a6
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

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