Hydrochloric Acid → (2S,3R)-3-(n-butyl)-2-hydroxysuccinic acid

HRID 1008280Notes

Reaction equation

HRID 1008280 reaction equation
C[O:2][C:3](=[O:15])[C@@H:4]([OH:14])[C@@H:5]([CH2:10][CH2:11][CH2:12][CH3:13])[C:6]([O:8]C)=[O:7].[OH-].[Na+].Cl>CO.O>[CH2:10]([C@@H:5]([C:6]([OH:8])=[O:7])[C@H:4]([OH:14])[C:3]([OH:15])=[O:2])[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23520166(2S,3R)-3-(n-butyl)-2-hydroxysuccinic dimethyl ester

Product 1

HCID 60111363(2S,3R)-3-(n-butyl)-2-hydroxysuccinic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To (2S,3R)-3-(n-butyl)-2-hydroxysuccinic dimethyl ester F-3 in methanol (28 mL) was added a solution of NaOH (2.2 g, 55 mmol) in water (28 mL). After 24 h the MeOH was removed, the crude reaction was acidified with HCl (6N, 12 mL) to pH=1, and then extracted with ethyl acetate (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated to give (2S,3R)-3-(n-butyl)-2-hydroxysuccinic acid F-4 (1.96 g, 90%).

Workup

  1. customAfter 24 h the MeOH was removed
  2. customthe crude reaction
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9742c6bdd16f48bf805aa22793aa50aa
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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