HCID 131728425, compound → HCID 131728424, compound

HRID 1172339Notes

Reaction equation

HRID 1172339 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([N+:15]([O-])=O)[CH2:13][C:12]([CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][C@H:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20]2)=[CH:11][CH2:10]1>CO.C(O)(=O)C.[Zn]>[NH2:15][C@@H:14]1[CH2:13][C:12]([CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][C@H:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20]2)=[CH:11][CH2:10][C@H:9]1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 131728425HCID 131728425, compound

Product 1

HCID 131728424HCID 131728424, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of Example 17A (75 mg, 0.16 mmol) in a mixture of methanol/acetic acid (1.0 mL/1.0 mL), Zn powder (170 mg, 2.60 mmol) was added at room temperature. The reaction mixture was stirred for thirty minutes, filtered, concentrated under reduced pressure and purified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (60 mg, 86%). MS (DCI) m/z 411 (M+H)+.

Workup

  1. additionwas added at room temperature
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-06a3a72845b841878d543ee6bc82aa26
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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