Sodium Bicarbonate → HCID 86737869, compound

HRID 1277714Notes

Reaction equation

HRID 1277714 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:24])[C@H:12]2[C@H:15]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:16])[C:9]=1[C:25]([O:27]CC1C=CC([N+]([O-])=O)=CC=1)=[O:26])(=[O:3])[CH3:2].C(=O)([O-])O.[Na+:42]>O1CCOCC1.O.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:24])[C@H:12]2[C@H:15]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:16])[C:9]=1[C:25]([O-:27])=[O:26])(=[O:3])[CH3:2].[Na+:42]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 56606519HCID 56606519, compound

Product 1

HCID 86737869HCID 86737869, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

p-Nitrobenzyl (5R,6S)-3-(2-acetamidoethylthio)-6-[(R)-1-phenylthioethyl]-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylate (e 103) (10 mg) in a mixture of dioxan and water (7:3, 5 ml) was added to 5% palladium on carbon catalyst which had been prehydrogenated for 30 min. in a mixture of dioxan and water (7:3, 5 ml). The mixture was hydrogenated at slightly super-atmospheric pressure for 4 hr., when sodium hydrogen carbonate (1.9 mg) was added to the mixture. The catalyst was filtered off and washed with water (5 ml). The filtrate was evaporated in vacuo to remove most of the dioxan and the resultant mixture was diluted with water to 25 ml and extracted with ethyl acetate. The aqueous extract was washed with ethyl acetate. The u.v. spectrum of the aqueous layer showed a maximum of about 300 nm, indicating the presence of the sodium salt. The volume of the aqueous solution was reduced to about 1 ml, loaded onto a Biogel P-2 column and eluted with water to give sodium (5R,6S)-3-(2-acetamidoethylthio)-6-[(R)-1-phenylthioethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e 104).

Workup

  1. customfor 4 hr
  2. filtrationThe catalyst was filtered off
  3. washwashed with water (5 ml)
  4. customThe filtrate was evaporated in vacuo
  5. customto remove most of the dioxan
  6. additionthe resultant mixture was diluted with water to 25 ml
  7. extractionextracted with ethyl acetate
  8. extractionThe aqueous extract
  9. washwas washed with ethyl acetate
  10. washeluted with water

Sources & evidence

ORD record
ord-7608dc9cc7384f0690dc26924d61f2b2
Source dataset
uspto-grants-1981_07
Patent number
US04278686

Reaction notes

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