3-Mercaptopropionic Acid → HCID 24693400, compound

HRID 1364187Notes

Reaction equation

HRID 1364187 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].C[O-].[Na+].Br[CH2:11][C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:13]>CO>[CH2:15]([N:14]([CH2:17][CH3:18])[C:12]([CH2:11][S:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 65143-Mercaptopropionic AcidHCID 2255452-bromo-N,N-diethylacetamideHCID 10942334Sodium Methoxide

Product 1

HCID 24693400HCID 24693400, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To 3-mercaptopropionic acid (200 mg, 1.884 mmol) in methanol (3 mL) are added sodium methoxide (204 mg, 3.768 mmol) and 2-Bromo-N,N-diethyl-acetamide (402 mg, 2.070 mmol). After stirring at 80° C. during 4 h and evaporation of solvent, the residue is treated with ethyl acetate and water, the pH is adjusted to 10 with an aqueous NaHCO3 solution and the aqueous phase is extracted with ethyl acetate. After acidification of the aqueous phase to pH 2 with an aqueous 1N HCl solution, it is extracted with ethyl acetate, then the organic phase is dried and evaporated to give the title compound.

Workup

  1. customevaporation of solvent
  2. additionthe residue is treated with ethyl acetate and water
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. extractionAfter acidification of the aqueous phase to pH 2 with an aqueous 1N HCl solution, it is extracted with ethyl acetate
  5. customthe organic phase is dried
  6. customevaporated

Sources & evidence

ORD record
ord-24edac1707a043d6827d073a7e0b9639
Source dataset
uspto-grants-2011_02
Patent number
US07888351B2

Reaction notes

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