Ethyl chloroformate → HCID 86610891, compound

HRID 902568Notes

Reaction equation

HRID 902568 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C@@H:5]([OH:9])[C:6]([OH:8])=[O:7].Cl.N[C@@H](C(O)=O)CCCN.[OH-].[Na+].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>CC(C)=O.O>[CH2:26]([O:25][C:23]([NH:1][CH2:2][CH2:3][CH2:4][C@@H:5]([OH:9])[C:6]([OH:8])=[O:7])=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 443122D-Ornithine monohydrochlorideHCID 22817059HCID 22817059, compound

Product 1

HCID 86610891HCID 86610891, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

In an amount of 15.3 g of (R)-5-amino-2-hydroxypentanoic acid, which was synthesized from (D)-ornithine hydrochloride according to the method described in YAKUGAKU ZASSHI (Vol 87, (1967), 1184-1188), was dissolved in 150 ml of a mixed solvent of acetone/water (1:1), added dropwise simultaneously with 45.8 ml of 5 N aqueous sodium hydroxide and 11 ml of ethyl chloroformate under ice cooling over 40 minutes, and stirred under the same condition for 1 hour. The reaction system was washed with ethyl acetate, then the aqueous layer was adjusted to pH 1 by slowly adding 10 N hydrochloric acid, and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, and filtered. Then, the filtrate was concentrated under reduced pressure to obtain 24.4 g of crude (R)-5-ethoxycarbonylamino-2-hydroxypentanoic acid. Physicochemical Properties of this Compound

Workup

  1. washThe reaction system was washed with ethyl acetate
  2. additionby slowly adding 10 N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThen, the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7939dbbe8a904bed9a0e51909320652a
Source dataset
uspto-grants-2008_04
Patent number
US07365174B2

Reaction notes

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