Sodium Bicarbonate → HCID 86739316, compound

HRID 1903707Notes

Reaction equation

HRID 1903707 reaction equation
[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:20])[C@@H:12]2[C@H:15]([O:17][CH:18]=[O:19])[CH3:16])[C:9]=1[C:21]([O:23]CC1C=CC([N+]([O-])=O)=CC=1)=[O:22])(=[O:3])[CH3:2].[H][H].C(=O)(O)[O-].[Na+:40]>O1CCOCC1.[Pd]>[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:20])[C@@H:12]2[C@H:15]([O:17][CH:18]=[O:19])[CH3:16])[C:9]=1[C:21]([O-:23])=[O:22])(=[O:3])[CH3:2].[Na+:40]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 12849735HCID 12849735, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86739316HCID 86739316, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The formate ester (e4, 10 mg) was dissolved in 30% aqueous 1,4-dioxan (10 ml) and shaken with hydrogen in the presence of 5% palladium on carbon catalyst (15 mg) for 3.5 hours. Sodium bicarbonate (2.3 mg) was then added and the solution filtered through Celite, washing well with water (20 ml). The filtrate was concentrated at reduced pressure to approximately 15 ml and washed with ethylacetate (3×20 ml). The resulting aqueous solution was estimated to contain 2.2 mg of the title compound (e7) based on εm 14,000 at λmax 307 nm in the uv spectrum,λmax (H2O) 307 nm 229 nm.

Workup

  1. filtrationthe solution filtered through Celite
  2. washwashing well with water (20 ml)
  3. concentrationThe filtrate was concentrated at reduced pressure to approximately 15 ml
  4. washwashed with ethylacetate (3×20 ml)

Sources & evidence

ORD record
ord-3077e0a91b6d46ab881a4ca29cc01005
Source dataset
uspto-grants-1984_03
Patent number
US04438036

Reaction notes

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