Dimethyl Sulfoxide → HCID 131710753, compound

HRID 1707186Notes

Reaction equation

HRID 1707186 reaction equation
FC(F)(F)C(O)=O.ClC(Cl)C([O:12][N:13]=[C:14]([C:51]1[S:52][CH:53]=[CH:54][CH:55]=1)[C:15]([NH:17][C@@H:18]1[C:49](=[O:50])[N:20]2[C:21]([C:33]([O:35]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:34])=[C:22]([CH2:25][S:26][C:27]3[S:28][C:29]([CH3:32])=[N:30][N:31]=3)[CH2:23][S:24][C@H:19]12)=[O:16])=O.CCOCC.CS(C)=O>C1(OC)C=CC=CC=1>[OH:12][N:13]=[C:14]([C:51]1[S:52][CH:53]=[CH:54][CH:55]=1)[C:15]([NH:17][C@@H:18]1[C:49](=[O:50])[N:20]2[C:21]([C:33]([OH:35])=[O:34])=[C:22]([CH2:25][S:26][C:27]3[S:28][C:29]([CH3:32])=[N:30][N:31]=3)[CH2:23][S:24][C@H:19]12)=[O:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 131710752HCID 131710752, compound

Product 1

HCID 131710753HCID 131710753, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (8 ml.) was added to a solution of the above ester (1.387 g.) in anisole (2 ml.) at 20°. After 5 minutes the solution was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. The solvent was evaporated and again the residue was dissolved in ethyl acetate. The solution was washed with water and then extracted with sodium bicarbonate solution. The combined extracts were washed with ethyl acetate, then taken to pH 1.9 with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and brine, dried and concentrated under reduced pressure to give a foam. Trituration with ether gave the title compound as a buff solid (0.50 g.), [α]D -84° (c 1, DMSO), λmax. (pH 6 buffer) 271.5 nm (ε 17,600), νmax. (Nujol) include 3250 (NH), 1780 (β-lactam), 2600+1710 (CO2H), and 1674+1548 cm.-1 (CONH), τ values (DMSO-d6) 0.24 (doublet, J 8 Hz; NH) 2.37 and 2.82 (thienyl protons) 4.12 (double doublet, J 5 and 8 Hz; C-7H), 4.76 (doublet, J 5 Hz; C-6H), 5.40 and 5.75 (2 doublets, branches of quartet, J 13 Hz; C-3 CH2), 6.13+6.40 (2 doublets, branches of quartet, J 18 Hz; C-2 CH2) and 7.29 (singlet; CH3).

Workup

  1. concentrationAfter 5 minutes the solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. customThe solvent was evaporated
  4. dissolutionagain the residue was dissolved in ethyl acetate
  5. washThe solution was washed with water
  6. extractionextracted with sodium bicarbonate solution
  7. washThe combined extracts were washed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water and brine
  10. customdried
  11. concentrationconcentrated under reduced pressure
  12. customto give a foam

Sources & evidence

ORD record
ord-d60220a6fcc7481dbe59d189c31a53ef
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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