Hydrochloric Acid → HCID 21352745, compound

HRID 395697Notes

Reaction equation

HRID 395697 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17]([O:19][CH2:20][CH2:21][O:22][CH:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]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:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17]([O:19][CH2:20][CH2:21][O:22][CH:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 53849663HCID 53849663, compound

Product 1

HCID 21352745HCID 21352745, compoundYield 180.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N1-(4-methoxybenzoyl)-N2-[2-[1-(tert-butoxycarbonyl)piperidin-4-yloxy]ethoxycarbonyl]-1,2-benzenediamine (180 mg, 0.362 mmol) in methylene chloride (2 mL) was treated with trifluoroacetic acid (0.30 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 phases were dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was taken up in methanol and treated with hydrochloric acid (gas,1-2 eq) and concentrated in vacuo yielding 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. dry with materialthe combined organic phases were dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5197c24f4dfd4266a39ae9326d013543
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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