Dimethyl Sulfoxide → HCID 86733038, compound

HRID 2398147Notes

Reaction equation

HRID 2398147 reaction equation
[CH3:1][C:2]1([CH3:18])[C@H:6]([C:7]([O-:9])=[O:8])[N:5]2[C:10](=[O:17])[C@@H:11]([NH:12][Si](C)(C)C)[C@H:4]2[S:3]1.C1OC1C.ClC(Cl)C([O:27][N:28]=[C:29]([C:33]1[O:34][CH:35]=[CH:36][CH:37]=1)[C:30](Cl)=[O:31])=O.CS(C)=O>ClCCl>[CH3:1][C:2]1([CH3:18])[C@H:6]([C:7]([OH:9])=[O:8])[N:5]2[C:10](=[O:17])[C@@H:11]([NH:12][C:30](=[O:31])[C:29](=[N:28][OH:27])[C:33]3[O:34][CH:35]=[CH:36][CH:37]=3)[C@H:4]2[S:3]1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 6378Propylene OxideHCID 54434434HCID 54434434, compoundHCID 86734755HCID 86734755, compound

Product 1

HCID 86733038HCID 86733038, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tirmethylsily 2,2-dimethyl-6β-trimethylsilylaminopenam-3α-carboxylate [prepared from the corresponding amino-acid (0.648 g.)] and propylene oxide (0.75 ml.) in dichloromethane (15 ml) was cooled to 0° and treated dropwise with a solution of 2-dichloroacetoxyimino(fur-2-yl)acetyl chloride [syn-isomer; prepared from the corresponding acid (0.579 g)] in dichloromethane (12 ml.). The resulting solution was maintained at 0° for 1 hour and was then evaporated to small volume and partitioned between ethylacetate and saturated sodium bicarbonate solution. The aqueous phase was washed with ethyl acetate, acidified with 2N=hydrochloric acid and extracted with ethyl acetate. The dried organic solution was evaporated to a small bulk and added dropwise to stirred petroleum spirit (b.p. 40°-60°). The resulting precipitate was collected, washed and dried to give the title acid (0.56 g., 55% based on amine), [α]D + 243° (c 0.93, DMSO), λmax. (pH 6 buffer) 275 nm (ε 9,600) νmax. (Nujol), 1778 (β-lactam), 1740 and 2600 (CO2H), 1670 and 1528 cm.-1 (CONH), τ (d6 -DMSO) values include 0.44 (d, J 6 Hz; NH) 2.18 and 3.34 (multiplets; aromatic protons), 5.70 (s; C-3H), 8.36 and 8.46 (2s; CH3 groups).

Workup

  1. temperaturewas cooled to 0°
  2. temperatureThe resulting solution was maintained at 0° for 1 hour
  3. customwas then evaporated to small volume
  4. custompartitioned between ethylacetate and saturated sodium bicarbonate solution
  5. washThe aqueous phase was washed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. customThe dried organic solution was evaporated to a small bulk
  8. additionadded dropwise
  9. customThe resulting precipitate was collected
  10. washwashed
  11. customdried
  12. customto give the title acid (0.56 g., 55% based on amine), [α]D + 243° (c 0.93, DMSO), λmax

Sources & evidence

ORD record
ord-783389f1de84458a9fe65f55127d405c
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

Loading…