Ethanol → (2R/S,4R)-methyl 2-(3,4-dihydroxyphenyl)thiazolidine-4-carboxylate

HRID 1748991Notes

Reaction equation

HRID 1748991 reaction equation
C(O)C.C([O-])(O)=O.[Na+].[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[OH:18])[CH:13]=O.Cl.[CH3:20][O:21][C:22](=[O:27])[C@H:23]([CH2:25][SH:26])[NH2:24]>O>[OH:9][C:10]1[CH:11]=[C:12]([CH:13]2[NH:24][C@H:23]([C:22]([O:21][CH3:20])=[O:27])[CH2:25][S:26]2)[CH:15]=[CH:16][C:17]=1[OH:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 87683,4-DihydroxybenzaldehydeHCID 516892Sodium BicarbonateHCID 2733208L-Cysteine, methyl ester, hydrochloride

Product 1

HCID 60194724(2R/S,4R)-methyl 2-(3,4-dihydroxyphenyl)thiazolidine-4-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a co-solvent of ethanol (5 mL) and water (5 mL), a solution including NaHCO3 (486 mg, 5.79 mmol), 3,4-dihydroxybenzaldhehyde (3,4-dihydroxybenzaldehyde) (800 mg, 5.80 mmol), and L-cysteine methyl ester hydrochloride (1.0 g, 5.84 mmol) was stirred at room temperature for 5 hours. After ethanol was evaporated, the reaction mixture was distributed between ethyl acetate and water, and an organic layer was dried, filtered, and evaporated. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (4:1) to obtain a solid Compound 104 (1.23 g, 83%).

Workup

  1. customAfter ethanol was evaporated
  2. customan organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d5f9d3b33c54cb1a34cb60fbd06071f
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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