Hydrochloric Acid → HCID 59392873, compound

HRID 222635Notes

Reaction equation

HRID 222635 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[Cl:40])[CH2:5][NH:6][C:7]([C:9]1[N:21]=[C:20]2[N:12]([O:13][C:14]3[C:19]2=[C:18]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:17]=[CH:16][CH:15]=3)[C:11](=[O:28])[C:10]=1[O:29]CC1C=CC=CC=1)=[O:8].Cl>ClCCl.[Fe](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[Cl:40])[CH2:5][NH:6][C:7]([C:9]1[N:21]=[C:20]2[N:12]([O:13][C:14]3[C:19]2=[C:18]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH:17]=[CH:16][CH:15]=3)[C:11](=[O:28])[C:10]=1[OH:29])=[O:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59392885HCID 59392885, compound

Product 1

HCID 59392873HCID 59392873, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent

Procedure

Iron(III) chloride (10 mg, 0.062 mmol) was added to a stirred solution of the product from Example 19.7 (12 mg, 0.021 mmol) in dichloromethane (5 mL). The mixture was stirred at room temperature for 1.5 h then aqueous hydrochloric acid (1.0 M) was added dropwise until the solution became clear. Products were extracted with ethyl acetate and the organic phase dried and concentrated in vacuo. The residue was recrystallized from a mixed solvent (hexane/ethyl acetate 10/1) to afford the desired compound (8 mg, 80%) as a gray solid.

Workup

  1. extractionProducts were extracted with ethyl acetate
  2. customthe organic phase dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from a mixed solvent (hexane/ethyl acetate 10/1)

Sources & evidence

ORD record
ord-5cabd4158b61420698eb13d31fb07f56
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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