Potassium Carbonate → HCID 12773835, compound

HRID 1577996Notes

Reaction equation

HRID 1577996 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C@@H:12]2[NH:16][C@H:15]([C:17]([OH:19])=[O:18])[CH2:14][CH2:13]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[OH-].[Na+].Br[CH2:23][CH2:24][C:25](Cl)=[O:26].[C:28]([O-:31])(=[S:30])[CH3:29].[K+].S1C=CC=C1CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[C:28]([S:30][CH2:23][CH2:24][C:25]([N:16]1[C@@H:12]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=2)[CH2:13][CH2:14][C@H:15]1[C:17]([OH:19])=[O:18])=[O:26])(=[O:31])[CH3:29]

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide2×HCID 159702-Thiopheneacetic acidHCID 84944Propanoyl chloride, 3-bromo-HCID 12773830HCID 12773830, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 12773835HCID 12773835, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
25 °C

Procedure

To a solution of cis-5-(3,4-dimethoxyphenyl)proline hydrochloride (8.0 g., 0.028 m) and sodium hydroxide (2.22 g., 0.055 m) in water (50 ml.) at 10° C., was slowly added 3-bromopropionyl chloride (2.80 ml., 0.028 m) along with sodium hydroxide (1.11 g., 0.028 m) in water (25 ml.), keeping pH between 7.5 and 9. This mixture was stirred at 25° C. overnight. Potassium thioacetate, prepared by mixing thiolacetic acid (1.50., 0.021 m) and potassium carbonate (1.75 g., 0.012 m) in water (15 ml.) was added to the reaction which was stirred overnight at 25° C. to afford the title compound, which was employed without isolation as the reactant in the following example.

Workup

  1. customat 10° C.
  2. additionwas added to the reaction which
  3. stirringwas stirred overnight at 25° C.

Sources & evidence

ORD record
ord-20d74a59b18943fabe989e107ea81f58
Source dataset
uspto-grants-1981_09
Patent number
US04290952

Reaction notes

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