HCID 12082527, compound → HCID 11772480, compound

HRID 1167371Notes

Reaction equation

HRID 1167371 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][C@@H:9]([CH2:12][O:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10][O:11][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:24]([O-])=O.Cl.C(O)(C)C.[H][H]>CO.[Pd]>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([O:13][CH2:12][CH:9]2[O:8][C:7]3[C:2]([NH2:1])=[C:3]([NH2:24])[CH:4]=[CH:5][C:6]=3[O:11][CH2:10]2)(=[O:16])=[O:15])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 12082527HCID 12082527, compoundHCID 21912024Isopropanol hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 11772480HCID 11772480, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Toluene-4-sulfonic acid (2R)-8-amino-7-nitro-2,3-dihydro-benzo(1,4)-dioxin-2-ylmethyl ester (4.1 g, 11 mmole) was dissolved in 200 mL of methanol to which 0.50 g of 10% palladium on carbon had been added. 4 N isopropanol HCl (10 mL) was then added and the mixture treated with 60 psi of hydrogen on a Parr apparatus overnight. The mixture was filtered through celite and concentrated in vacuum to give 4.6 g of the (R)-enantiomer of the title compound as a pink solid (m.p. 178-180° C.).

Workup

  1. additionhad been added
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-a395fe1c02534cf6bb7e5370887ee6d6
Source dataset
uspto-grants-2003_09
Patent number
US06617327B2

Reaction notes

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