Hydrochloric Acid → HCID 21352744, compound

HRID 427545Notes

Reaction equation

HRID 427545 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17]([O:19][CH2:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17]([O:19][CH2:20][CH2:21][CH:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 53736219HCID 53736219, compound

Product 1

HCID 21352744HCID 21352744, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N1-(4-methoxybenzoyl)-N2-[2-[1-(tert-butoxycarbonyl)piperidin-4-yl]ethoxycarbonyl]-1,2-benzenediamine (312 mg, 0.627 mmol) in methylene chloride (3 mL) was treated with trifluoroacetic acid (0.48 mL). After 0.5 h, the mixture was concentrated in vacuo. The residue was treated with 1 N aqueous sodium hydroxide followed by ethyl acetate. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were dried and concentrated in vacuo. The residue was taken up in methanol and treated with hydrochloric acid (gas, 1-2 eq) and concentrated in vacuo to yield the hydrochloride salt of the title compound (270 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was treated with 1 N aqueous sodium hydroxide
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. customthe combined organic layers were dried
  5. concentrationconcentrated in vacuo
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec63512ffd76426e817a4649939cb813
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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