Hydrochloric Acid → HCID 53785237, compound

HRID 597487Notes

Reaction equation

HRID 597487 reaction equation
[OH:1][C@@H:2]1[CH2:7][N:6]2[C:8](=[O:20])[C@@H:9]([NH:10][C:11](=[O:19])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:5]2[S:4][CH2:3]1.O1CCCC1.Cl>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][N:6]2[C:8](=[O:20])[C@@H:9]([NH:10][C:11](=[O:19])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:5]2[S:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 54466737HCID 54466737, compound

Product 1

HCID 53785237HCID 53785237, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (3R,6R,7R)-3-hydroxy-7-phenylacetamidocepham (0.5 g., 1.72 mmole) in anhydrous acid-free methylene chloride (15 ml.) containing anhydrous tetrahydrofuran (3 ml.) was treated with a solution of chromium trioxide/pyridine complex (1.3 g., 3 equivalents) in methylene chloride 30 ml.) at 21° for 1 hour. The reaction mixture was poured into excess dilute hydrochloric acid. After separation, the organic phase was washed with water, dried, and evaporated to an oil. Trituration with ethyl acetate and ether gave the title compound (0.095 g., 19% m.p. 174° to 177° (cap.) νmax. (bromoform, Unicam) 3430 (NH), 1770 (β-lactam), 1735 (ketone), 1678 and 1515 cm.- 1 (amide).

Workup

  1. customAfter separation
  2. washthe organic phase was washed with water
  3. customdried
  4. customevaporated to an oil

Sources & evidence

ORD record
ord-13b31dfa66d4490288ab0ab329c29d3d
Source dataset
uspto-grants-1977_03
Patent number
US04014872

Reaction notes

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