2-(morpholinomethyl)prop-2-yl (2S)-2-(benzyloxycarbonylamino)-4-methylsulfanylbutyrate → 2-(morpholinomethyl)prop-2-yl (2S)-2-amino-4-methylsulfanylbutyrate

HRID 1251880Notes

Reaction equation

HRID 1251880 reaction equation
C(OC([NH:11][C@@H:12]([CH2:26][CH2:27][S:28][CH3:29])[C:13]([O:15][C:16]([CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)([CH3:18])[CH3:17])=[O:14])=O)C1C=CC=CC=1>O.[Pd]>[NH2:11][C@@H:12]([CH2:26][CH2:27][S:28][CH3:29])[C:13]([O:15][C:16]([CH2:19][N:20]1[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1)([CH3:18])[CH3:17])=[O:14]

Participants

4

Reactant 1

HCID 865851352-(morpholinomethyl)prop-2-yl (2S)-2-(benzyloxycarbonylamino)-4-methylsulfanylbutyrate

Product 1

HCID 865851362-(morpholinomethyl)prop-2-yl (2S)-2-amino-4-methylsulfanylbutyrateYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of HCO2NH4 (5.6 g, 88.5 mmol) in water (10 ml) was added dropwise to a suspension of compound 2-(morpholinomethyl)prop-2-yl (2S)-2-(benzyloxycarbonylamino)-4-methylsulfanylbutyrate (7.5 g, 17.7 mmol) and 10% palladium on carbon (7.5g) in DMP (80 ml). The mixture was stirred at ambient temperature for 18 h. After filtration through Celite, the titrate was evaporated to dryness, neutralised with ammonia in diethyl ether to pH 9 and extracted with more ether. After evaporation the compound was purified by flash column chromatography eluting with a gradient of 1-5% ethanol/dichloromethane to give 2-(morpholinomethyl)prop-2-yl (2S)-2-amino-4-methylsulfanylbutyrate (50%).

Workup

  1. filtrationAfter filtration through Celite
  2. customthe titrate was evaporated to dryness
  3. extractionextracted with more ether
  4. customAfter evaporation the compound
  5. customwas purified by flash column chromatography
  6. washeluting with a gradient of 1-5% ethanol/dichloromethane

Sources & evidence

ORD record
ord-98975cb8db534df79986f18c2cff472e
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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