Hydrochloric Acid → HCID 14854210, compound

HRID 329794

Reaction equation

HRID 329794 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:29](=[O:30])[N:11]2[C:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:13]([C:16]([O:18]CC=C)=[O:17])[CH2:14][CH2:15][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[SnH](CCCC)(CCCC)CCCC.Cl>CC#N.CCOCC.O.C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:29](=[O:30])[N:11]2[C:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:13]([C:16]([OH:18])=[O:17])[CH2:14][CH2:15][C@H:10]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5948TributylstannaneHCID 11776TriphenylphosphineHCID 14281586HCID 14281586, compound

Product 1

HCID 14854210HCID 14854210, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 21885917Acetonitrile etherSolvent

Conditions

Temperature
0 °C

Procedure

To 700 mg (1.657 mMol) of 4-t-butyl 7β-t-butyloxycarbonylamino-3-allyloxycarbonyl-1-carba-3-cephem-4-carboxylate, dissolved in 12 ml of (1:1) CH3CN/(CH3CH2)2O, was added 174 mg (0.663 mMol) of triphenylphosphine and 20.34 mg (0.0829 mMol) of ##STR153## The reaction mixture was stirred for approximately 20 minutes and then cooled to 0° C. and treated with 0.464 ml (1.724 l) of (CH3CH2CH2CH2)3SnH. The reaction mixture was then allowed to cool and stirring was continued for 50 minutes. The crude reaction mixture was then treated with 1N HCl. This mixture was then poured into 100 ml of CHCl3 and 25 ml of H2O. The organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated, under reduced pressure to provide an oily solid. The crude product was recrystallized from CH2Cl2 /hexane to yield 570 mg (90%) of the title compound.

Workup

  1. temperatureto cool
  2. stirringstirring
  3. waitwas continued for 50 minutes
  4. customThe crude reaction mixture
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated, under reduced pressure
  9. customto provide an oily solid
  10. customThe crude product was recrystallized from CH2Cl2 /hexane

Sources & evidence

ORD record
ord-8c4ecdf71a2946e985d12e9cb2ad5e2c
Source dataset
uspto-grants-1990_01
Patent number
US04892942

Linked notes

Loading…