Formic Acid → HCID 21051845, compound

HRID 2214073Notes

Reaction equation

HRID 2214073 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:10]([CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].C(O)=[O:22].OO.S([O-])([O-])=O.[Na+].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:10]([CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:9])=[O:22]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 21051852HCID 21051852, compound

Product 1

HCID 21051845HCID 21051845, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2(R)-(3-chloro-4-methylsulfanyl-phenyl)-3-(2-oxo-cyclopentyl)-propionic acid (683.2 mg, 2.18 mmol), formic acid (2.47 mL, 65.5 mmol), and water (0.41 mL) cooled to 0° C. was treated with a 30% aqueous hydrogen peroxide solution (1.11 mL, 10.9 mmol). The reaction was stirred at 0° C. for 1 h. At this time, the reaction was treated with a saturated aqueous sodium sulfite solution. The resulting solution was poured into water (50 mL) and was then extracted into methylene chloride (3×50 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2(R)-(3-chloro-4-methanesulfinyl-phenyl)-3-(2-oxo-cyclopentyl)-propionic acid (724 mg, 100%) as a white foam: EI-HRMS m/e calcd for C15H17ClO4S (M+Na)+ 351.0428, found 351.0433.

Workup

  1. extractionwas then extracted into methylene chloride (3×50 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68293d2557964a4e953c437dbeb7cc2d
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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