Dimethylformamide → HCID 141560924, compound

HRID 1591264Notes

Reaction equation

HRID 1591264 reaction equation
[NH2:1][CH:2]1[C:32](=[O:33])[N:4]2[C:5]([C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[C:6]([C:9]3[C:12](=[O:13])[C:11](=[O:14])[C:10]=3[CH3:15])[CH2:7][S:8][C@H:3]12.[NH2:34][C:35]1[S:36][CH:37]=[C:38](/[C:40](=[N:50]/[O:51][CH3:52])/[C:41](N2C(=S)N(C)N=N2)=[O:42])[N:39]=1.CN(C)C=O>O1CCCC1.C(OCC)(=O)C>[NH2:34][C:35]1[S:36][CH:37]=[C:38](/[C:40](=[N:50]/[O:51][CH3:52])/[C:41]([NH:1][CH:2]2[C:32](=[O:33])[N:4]3[C:5]([C:16]([O:18][CH:19]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[O:17])=[C:6]([C:9]4[C:12](=[O:13])[C:11](=[O:14])[C:10]=4[CH3:15])[CH2:7][S:8][C@H:3]23)=[O:42])[N:39]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 14864656HCID 14864656, compoundHCID 88467418HCID 88467418, compound

Product 1

HCID 141560924HCID 141560924, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of diphenylmethyl 7-amino-3-(3,4-dioxo-2-methyl-1-cyclobutenyl)-3-cephem-4-carboxylate (100 mg, 0.217 mmol) and 1-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetyl]-4-methyltetrazole-5-thione (65 mg, 0.217 mmol) in tetrahydrofuran (1 mL) was stirred at 5° C. for 0.25 hr and then for 1 hr at 22° C. when N,N-dimethylformamide (0.05 mL) was added. The solution was diluted with ethyl acetate. The solution was sequentially washed with dilute aqueous NaHCO3 (2×), H2O, and saturated NaCl and then was dried over Na2SO4. Removal of the solvent left a yellow solid which was chromatographed on SiO2 (6 g) with methylene chloride/2-propanol (96:4) to afford the title compound (120 mg, 86% yield) as a yellow powder.

Workup

  1. washThe solution was sequentially washed with dilute aqueous NaHCO3 (2×), H2O, and saturated NaCl
  2. dry with materialwas dried over Na2SO4
  3. customRemoval of the solvent
  4. waitleft a yellow solid which
  5. customwas chromatographed on SiO2 (6 g) with methylene chloride/2-propanol (96:4)

Sources & evidence

ORD record
ord-6c42440dab674c0390165e8e726e71c5
Source dataset
uspto-grants-1993_04
Patent number
US05206360

Reaction notes

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