HCID 67673832, compound → HCID 58430309, compound

HRID 1585511Notes

Reaction equation

HRID 1585511 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]2[C@H:12]([CH2:13][CH2:14][C:15]=1[CH2:16][OH:17])[C@H:11]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]2=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[C:1]([O:5][C:6]([C:8]1[N:9]2[C@H:12]([CH2:13][CH2:14][C:15]=1[CH:16]=[O:17])[C@H:11]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]2=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67673832HCID 67673832, compound

Product 1

HCID 58430309HCID 58430309, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst3×HCID 6344DichloromethaneSolvent

Procedure

A solution of 194 g (0.52 Mol) of (6R, 7S)-7-tert-butoxycarbonylamino-3-hydroxy-methyl-8-oxo-1-aza-bicyclo[4.2.0]-oct-2-ene-2-carboxylic acid tert-butyl ester (9) in 4.85 l of methylene chloride was stirred with 455 g (0.52 Mol) manganese(IV) oxide at 22-25° C. for 15 h. Another 45.5 g manganese(IV) oxide was added and stirring was continued for 24 h. A further 45.5 g of manganese(IV) oxide was added and stirring was continued for 3.5 h. The solids were removed by filtration over 500 g dicalite and washed with 3 l methylene chloride. The combined filtrates were concentrated under aspirator vacuum and dried at 0.1 torr at 40° C. The residue was dissolved in 182 ml methylene chloride, diluted with 730 ml of pentane and stirred at room temperature for 30 min. The resulting solid was collected by filtration, washed with 140 ml pentane and dried at 0.1 torr at 40° C. to yield 158.5 g (6R, 7S)-7-tert-butoxycarbonylamino-3-formyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (10) as colorless crystals (83% Th.); m.p.: 194-195° C.

Workup

  1. stirringstirring
  2. waitwas continued for 3.5 h
  3. customThe solids were removed by filtration over 500 g dicalite
  4. washwashed with 3 l methylene chloride
  5. concentrationThe combined filtrates were concentrated under aspirator vacuum
  6. customdried at 0.1 torr at 40° C
  7. dissolutionThe residue was dissolved in 182 ml methylene chloride
  8. additiondiluted with 730 ml of pentane
  9. stirringstirred at room temperature for 30 min
  10. filtrationThe resulting solid was collected by filtration
  11. washwashed with 140 ml pentane
  12. customdried at 0.1 torr at 40° C.

Sources & evidence

ORD record
ord-a7fa40d40ad448718f9191271940eadb
Source dataset
uspto-grants-1999_08
Patent number
US05939410

Reaction notes

Loading…