Formic Acid → HCID 10965803, compound
Reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18](=[O:22])[C:19]([OH:21])=[O:20])([O-:10])=[O:9].C(O)=O>>[OH:22][C@@H:18]([CH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N+:8]([O-:10])=[O:9])[C:19]([OH:21])=[O:20]Participants
Conditions
- Temperature
- 40 °C
Procedure
Into 0.27 ml (19 mmol) of triethylamine was dissolved 3 mg (0.0048 mmol) of [RuCl((S,S)-TsDPEN)(p-cymene)] to prepare a solution, and to the solution were added 1.0 g (4.8 mmol) of o-nitrophenyl pyruvic acid and 0.54 ml (14 mmol) of formic acid, followed by stirring for 2 hours at a bath temperature of 40° C. Upon completion of the reaction, the solvent was distilled off under reduced pressure. Thereto was added 2 ml of water, and then 1 g of concentrated hydrochloric acid was gradually dropwise added under ice cooling, and pH of the solution was adjusted to 2. Extraction was performed twice with 10 ml of ethyl acetate, and then the organic phase was washed with 2 ml of a saturated aqueous solution of sodium chloride, followed by concentration under reduced pressure. As a result, 1.4 g (yield 97%, 95% ee) of (2S)-hydroxy-3-(o-nitrophenyl)propanoic acid was obtained.
Workup
- customto prepare a solution
- customUpon completion of the reaction
- distillationthe solvent was distilled off under reduced pressure
- additionThereto was added 2 ml of water
- addition1 g of concentrated hydrochloric acid was gradually dropwise added under ice cooling
- extractionExtraction
- washthe organic phase was washed with 2 ml of a saturated aqueous solution of sodium chloride
- concentrationfollowed by concentration under reduced pressure
Sources & evidence
- ORD record
- ord-cd76c5aff5a54ffca587e3055bdb3bd5
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08058471B2
Reaction notes
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