Hydrochloric Acid → HCID 11572211, compound

HRID 2112284Notes

Reaction equation

HRID 2112284 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:10][C@H:11]([C:13]([OH:15])=O)[CH3:12])[CH2:7][CH2:8][CH3:9])=[O:5])[CH3:2].Cl.P(Cl)(Cl)(Cl)(Cl)[Cl:18]>CCCCCC>[CH2:1]([O:3][C:4]([C@@H:6]([NH:10][C@H:11]([C:13]([Cl:18])=[O:15])[CH3:12])[CH2:7][CH2:8][CH3:9])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

Product 1

HCID 11572211HCID 11572211, compoundYield 115.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a slurry of N-[1-(S)-ethoxycarbonyl-1-butyl]-(S)-alanine (III, 1.5 g, 0.0069 moles) in n-hexane (10 ml) was purged dry hydrogen chloride gas at 25-30° C. under agitation. To this was added finely grounf phosphorous pentachloride (1.8 g, 0.0086 moles) in four lots, each after an interval of 10 mns. After the complete addition the reaction mixture was agitated for 1.5 hrs. The solid precipitated was filtered, washed with hexane to give 1.88 g of the title compound (I).

Workup

  1. additionAfter the complete addition the reaction mixture
  2. customThe solid precipitated
  3. filtrationwas filtered
  4. washwashed with hexane

Sources & evidence

ORD record
ord-80ed5a34bc9e403aa9021f8c3dca18be
Source dataset
uspto-grants-2009_04
Patent number
US07521566B2

Reaction notes

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