HCID 86594982, compound → (2S)-2-Amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl ester

HRID 1759715Notes

Reaction equation

HRID 1759715 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:20]=[CH:19][C:9]([C:10]([NH:12][CH2:13][C@@H:14]([C:16]([O-:18])=[O:17])[NH2:15])=[O:11])=[CH:8][CH:7]=1>C1COCC1.C1CCCCC=1.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:20]=[CH:19][C:9]([C:10]([NH:12][CH2:13][C@@H:14]([C:16]([O:18][C:6]([CH3:20])([CH3:7])[CH3:5])=[O:17])[NH2:15])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 86594982HCID 86594982, compound

Product 1

HCID 15550489(2S)-2-Amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolventHCID 8079CyclohexeneSolvent

Procedure

128 mg of Pd(OH)2 on carbon is added to a solution of 10-4 (1.28 g, 2.64 mmol) in 35 ml of THF and 10 ml of cyclohexene, and the reaction medium is heated under reflux for 45 minutes. The temperature is brought down to approximately 20° C. followed by filtering, rinsing with ethyl acetate and evaporating under reduced pressure until a dry extract is obtained (724 mg) corresponding to the expected deprotected product.

Workup

  1. temperaturethe reaction medium is heated
  2. temperatureunder reflux for 45 minutes
  3. customis brought down to approximately 20° C.
  4. filtrationby filtering
  5. washrinsing with ethyl acetate
  6. customevaporating under reduced pressure until a dry
  7. extractionextract
  8. customis obtained (724 mg) corresponding to the expected deprotected product

Sources & evidence

ORD record
ord-5293c37015cb486f93e6f18814bad488
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

Loading…