Acetic Acid → HCID 70635149, compound

HRID 1414678Notes

Reaction equation

HRID 1414678 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. glacial acetic acid and 48 ml. dimethylformamide and 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 (3×), 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 (3×), water, 1N
  3. dry with materialHCl, and brine and then dried (Na2SO4)
  4. customEvaporation to dryness in vacuo

Sources & evidence

ORD record
ord-d50f02e6557744308168e60f7bebde4c
Source dataset
uspto-grants-1977_01
Patent number
US04001226

Reaction notes

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