Hydrochloric Acid → Danosteine

HRID 538090Notes

Reaction equation

HRID 538090 reaction equation
C[O:2][C:3](=[O:12])[CH2:4][S:5][CH2:6][CH2:7][C:8]([O:10]C)=[O:9].O.[OH-].[Li+].Cl>C1COCC1.CO.O.O>[C:3]([CH2:4][S:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])([OH:12])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 81891Propanoic acid, 3-((2-methoxy-2-oxoethyl)thio)-, methyl esterHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 71205DanosteineYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 3-((2-methoxy-2-oxoethyl)thio)propanoate (5.0 g, 26 mmol) in THF/MeOH/water (60 mL, 4:1:1) was added lithium hydroxide monohydrate (4.375 g, 101 mmol). The resulting mixture was stirred at room temperature overnight before it was concentrated under reduced pressure. The residue obtained was diluted with water (˜100 mL) and the resulting solution was acidified with 6N HCl. The mixture was partitioned between water and ethyl acetate. The organic extract was washed with more water, separated, dried over sodium sulfate, filtered and evaporated to afford 3-((carboxymethyl)thio)propanoic acid (3.64 g, 85%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.55-2.57 (t, 2H) 2.75-2.79 (t, 2H) 3.27 (s, 2H) 12.41 (s, 2H)

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue obtained
  3. customThe mixture was partitioned between water and ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with more water
  6. customseparated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-347735c7de174143b9ed0b69f53a33d0
Source dataset
uspto-grants-2014_10
Patent number
US08865718B2

Reaction notes

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