Water → HCID 59867908, compound

HRID 1662733Notes

Reaction equation

HRID 1662733 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=1[O:23][CH3:24])(=[O:13])=[O:12])[C:6](=[O:25])[C:5]2([N:35]1[CH2:44][C@H:43]([OH:45])[CH2:42][C@H:36]1[C:37]([N:39]([CH3:41])[CH3:40])=[O:38])[C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=1[O:33][CH3:34].O>C(O)(=O)C.[Fe]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[C:5]([N:35]3[CH2:44][C@H:43]([OH:45])[CH2:42][C@H:36]3[C:37]([N:39]([CH3:41])[CH3:40])=[O:38])([C:26]3[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])[C:6]2=[O:25])(=[O:12])=[O:13])=[C:15]([O:23][CH3:24])[CH:16]=1

Participants

5

Reactant 2

HCID 962WaterHCID 59867937HCID 59867937, compound

Product 1

HCID 59867908HCID 59867908, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 450 mg of the compound obtained in Example 185 and 381 mg of iron in acetic acid (5 ml) was stirred at 80° C. for one hour. Water was added to the solution and the resulting mixture was extracted with EtOAc; the organic layer was washed with a saturated aqueous solution of NaHCO3 and with saturated brine, dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60N; mobile phase: CHCl3/MeOH=20/1 to 10/1; v/v) to obtain 301 mg of the title compound (amorphous).

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. washthe organic layer was washed with a saturated aqueous solution of NaHCO3 and with saturated brine
  3. dry with materialdried over Na2SO4
  4. customthe drying agent was separated by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by column chromatography (silicagel 60N; mobile phase: CHCl3/MeOH=20/1 to 10/1; v/v)

Sources & evidence

ORD record
ord-4b15201a155a4291aa425ff9d99197e9
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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