Hydrochloric Acid → 2(R)-(3-(Acetylthio)-2(S)-methyl-1-oxopropoxy)-3-(methylthio)propanoic acid

HRID 2226575Notes

Reaction equation

HRID 2226575 reaction equation
[C:1]([S:4][CH2:5][C@@H:6]([CH3:10])[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[C@@H:24]([CH2:28][S:29][CH3:30])[C:25]([OH:27])=[O:26].C(N(CC)CC)C.Cl>O1CCCC1>[C:1]([S:4][CH2:5][C@@H:6]([CH3:10])[C:7](=[O:9])[O:8][C@@H:24]([CH2:28][S:29][CH3:30])[C:25]([OH:27])=[O:26])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2724506D-beta-acetylthioisobutyric acidHCID 15647666(R)-2-hydroxy-3-(methylthio)propanoic acid

Product 1

HCID 102656742(R)-(3-(Acetylthio)-2(S)-methyl-1-oxopropoxy)-3-(methylthio)propanoic acidYield 15.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(S)-3-(Acetylthio)-2-methylpropanoic acid (0.38 g, 2.35 mmol) and 1,1'-carbonyldiimidazole (0.38 g, 2.35 mmol) were stirred under nitrogen, in tetrahydrofuran (10 ml). After 30 min, a solution of (R)-2-hydroxy-3-(methylthio)propanoic acid (0.32 g, 2.35 mmol), triethylamine (0.33 ml, 2.35 mmol) and tetrahydrofuran (10 ml) was added dropwise. The reaction mixture was stirred at 25° for 18 h before evaporation of the solvent. The residue was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic extracts were dried (Na2SO4) and the solvent evaporated. Chromatography on silica with dichloromethane/ethyl acetate as eluant gave the sub-title compound (0.1 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-d5a2eae0dd0145f8a3bf7310978c8aea
Source dataset
uspto-grants-1994_09
Patent number
US05348978

Reaction notes

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