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

HRID 1611245Notes

Reaction equation

HRID 1611245 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 B-3 in MeOH (28 mL) is added a solution of NaOH (2.2 g, 55 mmol) in water (28 mL). After 24 hours, the MeOH is removed, the crude reaction is acidified with HCl (6 N, 12 mL) to pH=1, and then extracted with EtOAc (3×50 mL). The combined organic layers are dried (Na2SO4) and concentrated to give (2S,3R)-3-(n-butyl)-2-hydroxysuccinic acid B-4.

Workup

  1. customthe MeOH is removed
  2. customthe crude reaction
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4002d8ebf87b4cf9bddcaa257fe11652
Source dataset
uspto-grants-2006_01
Patent number
US06987104B2

Reaction notes

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