Hydrochloric Acid → HCID 22866844, compound

HRID 1900170Notes

Reaction equation

HRID 1900170 reaction equation
Cl.N#N.C(OC([NH:11][C@H:12]([C:17]([NH:19][CH:20]([CH3:31])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=1)=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH:20]([NH:19][C:17](=[O:18])[C@H:12]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:11])[CH3:31])=[CH:28][CH:27]=1)#[N:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86749987HCID 86749987, compound

Product 1

HCID 22866844HCID 22866844, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Hydrogen chloride gas was introduced into a solution containing 15.0 g of N2 -tert-butoxycarbonyl-N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-isoleucinamide dissolved in 300 mL of methylene chloride for 1 hour at room temperature. After completion of the reaction, the methylene chloride was removed under reduced pressure, thus obtaining a crude crystal. 200 ml of a saturated aqueous solution of sodium bicarbonate and 200 ml of methylene chloride were added to the crude crystal, and the mixture was stirred for 30 minutes and extracted with methylene chloride. The organic layer was washed with water, and dried over anhydrous sodium sulfate. The methylene chloride was removed under reduced pressure. The obtained crude product was washed with acetone to afford 10.0 g of the desired product (yield: 90%). Melting point: 64°-67° C.

Workup

  1. customAfter completion of the reaction
  2. customthe methylene chloride was removed under reduced pressure
  3. customthus obtaining a crude crystal
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe methylene chloride was removed under reduced pressure
  8. customThe obtained crude product
  9. washwas washed with acetone

Sources & evidence

ORD record
ord-251d9f230d9b454b9a6bce89b5734de6
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Reaction notes

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