HCID 22479270, compound → HCID 22479223, compound

HRID 2182623Notes

Reaction equation

HRID 2182623 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[C:12]([C:14]1[CH:39]=[CH:38][C:17]([CH:18]([C:20]23[CH2:27][CH2:26][CH2:25][N:24]2[C:23](=[O:28])[N:22]([C:29]2[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=2)[C:21]3=[O:37])[OH:19])=[CH:16][CH:15]=1)#[N:13]>C(Cl)Cl>[C:12]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([C:20]23[CH2:27][CH2:26][CH2:25][N:24]2[C:23](=[O:28])[N:22]([C:29]2[CH:30]=[C:31]([Cl:36])[CH:32]=[C:33]([Cl:35])[CH:34]=2)[C:21]3=[O:37])=[O:19])=[CH:38][CH:39]=1)#[N:13]

Participants

4

Reactant 2

HCID 22479270HCID 22479270, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22479223HCID 22479223, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PCC (2.43 g) was added to a solution of the compound from Example 111 (3.90 g) in CH2Cl2 (20 mL) and the reaction mixture stirred at room temperature for 48 hours. The mixture was filtered though a plug of SiO2 (washing with 1:1 CH2Cl2:EtOAc). The solvent was evaporated and the residue was purified by chromatography (SiO2, hexanes to 1:1 hexanes/EtOAc gradient elution) providing the titled compound (1.97 g). MS (m/z) 414 (MH+). mp. 72.1° C.

Workup

  1. filtrationThe mixture was filtered though a plug of SiO2 (washing with 1:1 CH2Cl2:EtOAc)
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography (SiO2, hexanes to 1:1 hexanes/EtOAc gradient elution)

Sources & evidence

ORD record
ord-acfd58f066264abd9052be35d4b41a9d
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

Loading…