Acetic Acid → HCID 70635149, compound

HRID 596829Notes

Reaction equation

HRID 596829 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[CH:13]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:14]([C:17]([O:19]CCI)=[O:18])=[CH:15][S:16][C@H:11]12)=[O:8].C(O)(=O)C.CN(C)C=O>C(OCC)(=O)C.[Zn]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[CH:13]([C:23]([O:25][CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:24])[C:14]([C:17]([OH:19])=[O:18])=[CH:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 70635824HCID 70635824, compound

Product 1

HCID 70635149HCID 70635149, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzhydryl 7-(2-thienylacetamido)-3-(2-iodoethoxycarbonyl)-2-cephem-4-carboxylate (2.79 g., 4.05 mmol.) was dissolved in a mixture of 8 ml. of glacial acetic acid and 48 ml. dimethylformamide at 0° and was reacted with 2.79 g. zinc dust (10.5 eq.) for 1.5 hours. The reaction mixture was diluted with ethyl acetate and filtered through a celite filter. The filtrate was washed successively with sodium bicarbonate solution (3X), water, 1N.HCl, and brine and then dried (Na2SO4). Evaporation to dryness in vacuo gave 1.92 (89%) of benzhydryl 7-(2-thienylacetamido)-3-carboxy-2-cephem-4-carboxylate: nmr (CDCl3) δ3.84 (s, side chain CH2), 4.99 (d, 1, J = 4.0 Hz, C6 --H), 5.45 (m, C4 --H and C7 --H) and 7.80 (s, C2 --H).

Workup

  1. filtrationfiltered through a celite filter
  2. washThe filtrate was washed successively with sodium bicarbonate solution (3X), water, 1N
  3. dry with materialHCl, and brine and then dried (Na2SO4)
  4. customEvaporation to dryness in vacuo

Sources & evidence

ORD record
ord-2d9b89ae9ae740d78eedb15d002cd6a4
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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