Triethylamine → HCID 131723933, compound

HRID 1370734Notes

Reaction equation

HRID 1370734 reaction equation
[C:1]([NH:4][C:5](=[CH2:10])[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].[F:11][C:12]1[CH:17]=[CH:16][C:15](S)=[CH:14][CH:13]=1.C(N(CC)CC)C.O[O:27][S:28]([O-:30])=O.[K+]>CO.O>[C:1]([NH:4][C@H:5]([C:6]([O:8][CH3:9])=[O:7])[CH2:10][S:28]([C:15]1[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=1)(=[O:30])=[O:27])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 677894-FluorothiophenolHCID 98644Methyl 2-acetamidoacrylateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 131723933HCID 131723933, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of methyl 2-acetamidoacrylate (10.0 g, 69.9 mmol) in 100 mL of methanol, cooled to zero degrees C., was added 4-fluorothiophenol (7.44 mL, 69.9 mmol) followed by triethylamine (9.74 mL, 69.9 mmol). The mixture stirred under a nitrogen atmosphere for 4 hours. The solution was poured into a slurry of Oxone® (86 g, 140 mmol) in H2O (250 mL) and MeOH (125 mL). After stirring at room temperature for 18 hours, the mixture was partitioned between EtOAc (200 mL) and H2O and washed with saturated NaHCO3 (3×100 mL) and brine (1×100 mL). After concentration in vacuo, trituration with diethyl ether afforded the title compound as a white solid (16.3 g, 77%): MS MH+ calcd. for C12H14NO5SF: 304, found 304. HRMS calcd. for C12H14NO5SF: 303.0577, found: 303.0581.

Workup

  1. stirringAfter stirring at room temperature for 18 hours
  2. customthe mixture was partitioned between EtOAc (200 mL) and H2O
  3. washwashed with saturated NaHCO3 (3×100 mL) and brine (1×100 mL)
  4. concentrationAfter concentration in vacuo, trituration with diethyl ether

Sources & evidence

ORD record
ord-c5e87b6bfa0040a9a1c9ae1e0c5fc566
Source dataset
uspto-grants-2003_06
Patent number
US06583299B1

Reaction notes

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