HCID 131714276, compound → HCID 70390958, compound

HRID 371233Notes

Reaction equation

HRID 371233 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:18][O:19][C:20]([C@H:22]1[N:25]([S:26]([O-:29])(=[O:28])=[O:27])[C:24](=[O:30])[C@H:23]1[NH:31]C(OCC1C=CC=CC=1)=O)=[O:21]>CO.[Pd]>[NH2:31][C@H:23]1[C@@H:22]([C:20]([O:19][CH3:18])=[O:21])[N:25]([S:26]([OH:29])(=[O:27])=[O:28])[C:24]1=[O:30]

Participants

4

Reactant 1

HCID 131714276HCID 131714276, compound

Product 1

HCID 70390958HCID 70390958, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
-50 °C

Procedure

A solution of 186 mg of (cis)-4-(methoxycarbonyl)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt in 2 ml of methanol is hydrogenated over 10% palladium on charcoal (95 mg) for 1.5 hours at 1 atmosphere. The catalyst is filtered off and rinsed with dichloromethane and the filtrate is treated with 97% formic acid and cooled to -50° C. (the presence of a seed crystal at this stage is necessary to induce crystallization). After crystallization commences, the mixture is allowed to stand for about 16 hours at 10° C. The resulting solid is washed with dichloromethane, hexane, and dried in vacuo, yielding 50 mg of the title compound.

Workup

  1. filtrationThe catalyst is filtered off
  2. washrinsed with dichloromethane
  3. additionthe filtrate is treated with 97% formic acid
  4. customcrystallization)
  5. customAfter crystallization commences
  6. washThe resulting solid is washed with dichloromethane, hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e8c44d677df8493ca15c623c599c18e2
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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