HCID 21500060, compound → HCID 21500059, compound

HRID 596144Notes

Reaction equation

HRID 596144 reaction equation
[N+](C1C=CC(C[O:9][C:10]([CH:12]2[C:19]([Cl:21])([CH3:20])[CH2:18][S:17][CH:16]3[N:13]2[C:14](=[O:32])[CH:15]3[NH:22][C:23](=[O:31])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:11])=CC=1)([O-])=O>C(OCC)(=O)C.[Pd]>[Cl:21][C:19]1([CH3:20])[CH2:18][S:17][CH:16]2[N:13]([C:14](=[O:32])[CH:15]2[NH:22][C:23](=[O:31])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:12]1[C:10]([OH:11])=[O:9]

Participants

4

Reactant 1

HCID 21500060HCID 21500060, compound

Product 1

HCID 21500059HCID 21500059, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Chloro-3-methyl-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid p-nitrobenzyl ester (1.06 g, 2.1 mmoles) was hydrogenated in 60 ml of ethyl acetate over 1 g. of 10 per cent palladium on charcoal. The catalyst was filtered and washed with ethyl acetate. The filtrate was extracted with ice cold saturated sodium bicarbonate (100 ml.). The aqueous phase was covered with fresh ethyl acetate (100 ml.) and was acidified with concentrated hydrochloric acid to pH 1.5. The organic phase was separated, dried and flash concentrated to a total of 10 ml. The obtained solution was added to pentane to give 475 mg. (61 per cent yield) of the desired acid, which did not melt but slowly decomposed above 90° C., nmr (DMSO--D6) ppm (δ), 1.75 (s, 3, CH3), 3.32 (ABq, δ 0.675 ppm, J 14.2 cps, 2--CH2), ##STR9## 4.55 (s, 1, 4--H), 5.22 (2, 1, 6H), 5.51 (q, 1, 7H), 7.34 (s, 5, C6H5), 9.1 (d, 1, NH).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethyl acetate
  3. extractionThe filtrate was extracted with ice cold saturated sodium bicarbonate (100 ml.)
  4. customThe organic phase was separated
  5. customdried
  6. concentrationflash concentrated to a total of 10 ml
  7. additionThe obtained solution was added to pentane
  8. customto give 475 mg

Sources & evidence

ORD record
ord-96546b3b9245460bb9bcad772038e553
Source dataset
uspto-grants-1977_03
Patent number
US04010156

Reaction notes

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