Hydrochloric Acid → HCID 18665317, compound

HRID 2394320Notes

Reaction equation

HRID 2394320 reaction equation
Cl.N#N.C(OC([NH:11][C@H:12]([C:16]([NH:18][C:19]([CH3:31])([CH3:30])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=O)(C)(C)C>C(Cl)Cl>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][C:19]([NH:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH2:11])([CH3:30])[CH3:31])=[CH:27][CH:26]=1)#[N:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86753121HCID 86753121, compound

Product 1

HCID 18665317HCID 18665317, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride gas was introduced into a solution containing 3.7 g of N2 -tert-butoxycarbonyl-N1 -[2-(4-cyanophenoxy)-1,1-dimethylethyl]-L-valinamide dissolved in 50 ml of methylene chloride for 3 hours at room temperature. After the completion of the reaction, the methylene chloride was removed under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added to the residue. The organic layer in the residue was extracted with methylene chloride, washed with water, and then dried over anhydrous magnesium sulfate. The solvent in the organic layer was removed under reduced pressure, thus yielding 2.4 g of the desired product (yield: 87%).

Workup

  1. customAfter the completion of the reaction
  2. customthe methylene chloride was removed under reduced pressure
  3. additionA saturated aqueous solution of sodium bicarbonate was added to the residue
  4. extractionThe organic layer in the residue was extracted with methylene chloride
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent in the organic layer was removed under reduced pressure

Sources & evidence

ORD record
ord-20a04d29d5f648dba2e420fc6389c75b
Source dataset
uspto-grants-1998_09
Patent number
US05811424

Reaction notes

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