HCID 178470846, compound → HCID 178471902, compound

HRID 1802074Notes

Reaction equation

HRID 1802074 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:22]3)[CH:16]=2)[N:11]=1)([N+:7]([O-])=O)[CH3:6])[CH3:2]>C(O)(=O)C.C(#N)C.[Zn]>[CH2:1]([O:3][C:4](=[O:31])[C:5]([NH2:7])([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20][C@H:21]3[CH2:22][CH2:23][C@H:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:25][CH2:26]3)[CH:16]=2)[N:11]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 1

HCID 178470846HCID 178470846, compound

Product 1

HCID 178471902HCID 178471902, compoundYield 25.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

2-[6-(trans-4-tert-Butyl-cyclohexyloxy)-quinolin-2-yl]-2-nitro-propionic acid ethyl ester (76 mg, 0.00018 mol) was dissolved in acetic acid (1.0 mL, Fisher), and cooled in a 20° C. water bath, followed by addition of zinc (115 mg, 0.00176 mol, Aldrich) in small portions. After 2 h, the reaction was diluted with acetic acid and acetonitrile and filtered through a PTFE filter. The excess of solvents were removed under vacuum, and the residue was purified via preparative HPLC (10-90% acetonitrile with 0.1% TFA) to give a pure product (18 mg, 20%) as TFA salt.

Workup

  1. filtrationfiltered through a PTFE
  2. filtrationfilter
  3. customThe excess of solvents were removed under vacuum
  4. customthe residue was purified via preparative HPLC (10-90% acetonitrile with 0.1% TFA)

Sources & evidence

ORD record
ord-0f66b194bf2b42a6b5ff8e5807b5d363
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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