Hydrochloric Acid → HCID 178502900, compound

HRID 851567Notes

Reaction equation

HRID 851567 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:33])/[C:19](=[N:25]\[O:26][CH2:27][C:28](=[O:32])[NH:29][O:30][CH3:31])/[C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:34])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:41]([O:44][CH2:45]I)(=[O:43])[CH3:42].Cl>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:33])/[C:19](=[N:25]\[O:26][CH2:27][C:28](=[O:32])[NH:29][O:30][CH3:31])/[C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:34])[N:10]2[C:11]=1[C:12]([O:14][CH2:45][O:44][C:41](=[O:43])[CH3:42])=[O:13])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11820084Iodomethyl acetateHCID 12774332(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-[2-(methoxyamino)-2-oxoethoxy]iminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 178502900HCID 178502900, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(6R,7R)-3-Acetoxymethyl-7-[Z-2-methoxycarbamoylmethoxyimino-2-(fur-2-yl)acetamido]-ceph-3-em-4-carboxylic acid (992 mg) was dissolved in dry N,N-dimethylformamide (8 ml). Dried potassium carbonate (138 mg) was added and the mixture was stirred at 0°. Iodomethyl acetate (1.1 g) in a little dimethylformamide was added, stirring was continued at 0° for 1 hr, and the mixture was poured into hydrochloric acid (N, 50 ml) and extracted with ethyl acetate (3×50 ml). The ethyl acetate extracts were washed with N-hydrochloric acid (2×50 ml), water (100 ml) and saturated sodium hydrogen carbonate solution (2×30 ml), dried (Na2SO4) and evaporated. The residue in a little ethyl acetate was added dropwise to well-stirred light petroleum (b.p. 40°-60°), when the ester separated as an off-white powder, 513 mg, λmax (EtOH) 277.5 nm, νmax (Nujol) 3240 (--NH), 1786 (β-lactam), 1765, 1742 (acetate+--CO2CH2OCOCH3), 1680, 1540 cm-1 (--CONH--), τ(DMSOd6) 6.25 (--OCH3, 2--CH2 --), 5.38 (--O--CH2 --CO--), 2.01, 3.11, 3.22 (fur-2-yl), 0.18 (--CONH--), 4.05 (7H), 4.69 (6H), 4.99, 5.25 (3--CH2 --), 7.86, 7.96 (--COCH3), 4.09 (--OCH2O--).

Workup

  1. stirringstirring
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe ethyl acetate extracts were washed with N-hydrochloric acid (2×50 ml), water (100 ml) and saturated sodium hydrogen carbonate solution (2×30 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. additionThe residue in a little ethyl acetate was added dropwise
  7. stirringto well-stirred light petroleum (b.p. 40°-60°), when the ester
  8. customseparated as an off-white powder, 513 mg, λmax (EtOH) 277.5 nm, νmax (Nujol) 3240 (--NH), 1786 (β-lactam), 1765, 1742 (acetate+--CO2CH2OCOCH3), 1680, 1540 cm-1 (--CONH--), τ(DMSOd6) 6.25 (--OCH3, 2--CH2 --), 5.38 (--O--CH2 --CO--), 2.01, 3.11, 3.22 (fur-2-yl), 0.18 (--CONH--), 4.05 (7H), 4.69 (6H), 4.99, 5.25 (3--CH2 --), 7.86, 7.96 (--COCH3), 4.09 (--OCH2O--)

Sources & evidence

ORD record
ord-e6708fb450494a5887ff817f40cf1f0e
Source dataset
uspto-grants-1983_05
Patent number
US04385177

Reaction notes

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