Water → HCID 131719840, compound

HRID 54765Notes

Reaction equation

HRID 54765 reaction equation
[N+](C1C=CC(C[O:11][C:12]([C:14]2[N:15]3[CH:18]([CH:19]([CH3:32])[C:20]=2[S:21][CH:22]2[CH2:26][CH:25]([CH2:27][O:28][C:29]([NH2:31])=[O:30])[O:24][CH2:23]2)[CH:17]([CH:33]([OH:35])[CH3:34])[C:16]3=[O:36])=[O:13])=CC=1)([O-])=O.C(=O)(O)[O-].[Na+:41].O.[H][H]>[Pd].O1CCOCC1>[Na+:41].[NH2:31][C:29]([O:28][CH2:27][CH:25]1[O:24][CH2:23][CH:22]([S:21][C:20]2[CH:19]([CH3:32])[CH:18]3[N:15]([C:16](=[O:36])[CH:17]3[CH:33]([OH:35])[CH3:34])[C:14]=2[C:12]([O-:13])=[O:11])[CH2:26]1)=[O:30]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 131719841HCID 131719841, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131719840HCID 131719840, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.181 g of product from Example 17, 0.032 g of sodium bicarbonate, 2 ml of water, 11 ml of dioxane and 0.100 g of 10% palladium/carbon is reduced in a Parr apparatus at 42 psi of hydrogen for 3 hours. The reaction mixture is filtered through a pad of diatomaceous earth, washed with water and concentrated to 1/2 volume. The solution is extracted with ethyl acetate and the aqueous layer is freeze-dried. The product is purified using C18 reverse phase chromatography (95/5 water/ethyl alcohol) to give 0.095 g of the desired product as a yellow solid.

Workup

  1. filtrationThe reaction mixture is filtered through a pad of diatomaceous earth
  2. washwashed with water
  3. concentrationconcentrated to 1/2 volume
  4. extractionThe solution is extracted with ethyl acetate
  5. customthe aqueous layer is freeze-dried
  6. customThe product is purified

Sources & evidence

ORD record
ord-40080d24e98f4a2ba5a5df443010b0d3
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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