Ethyl Acetate → D-Alloisoleucine, methyl ester

HRID 1019662Notes

Reaction equation

HRID 1019662 reaction equation
Cl.[NH2:2][C@@H:3]([C:8]([O:10][CH3:11])=[O:9])[C@H:4]([CH2:6][CH3:7])[CH3:5].C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:2][C@@H:3]([C:8]([O:10][CH3:11])=[O:9])[C@H:4]([CH2:6][CH3:7])[CH3:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12890355D-Alloisoleucine, methyl ester, hydrochloride (1:1)2×

Product 1

HCID 6950463D-Alloisoleucine, methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

methyl d-alloisoleucinate hydrochloride (Compound 2) was charged to ethyl acetate. A solution of potassium carbonate in water was then added. The mixture was then stirred vigorously at room temperature for 1 hour. The two layers were separated and the aqueous layer further extracted with ethyl acetate. The organic layers were combined and washed with brine. The organic layers were then concentrated in vacuo and filtered to yield methyl D-alloisoleucinate (Compound 3) as a pale yellow oil.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer further extracted with ethyl acetate
  3. washwashed with brine
  4. concentrationThe organic layers were then concentrated in vacuo
  5. filtrationfiltered

Sources & evidence

ORD record
ord-aa5b49271b974048a7b916eb1d69cd63
Source dataset
uspto-grants-2014_05
Patent number
US08716286B2

Reaction notes

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