HCID 178418361, compound → HCID 178475078, compound

HRID 658441Notes

Reaction equation

HRID 658441 reaction equation
[C:1]([NH:4]/[C:5](=[CH:9]\[CH2:10][PH:11]([CH2:13][OH:14])=[O:12])/[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[H][H]>CO>[C:1]([NH:4][C@@H:5]([CH2:9][CH2:10][PH:11]([CH2:13][OH:14])=[O:12])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 178418361HCID 178418361, compound2×HCID 178474814HCID 178474814, compound

Product 1

HCID 178475078HCID 178475078, compoundYield 612.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-2-acetylamino-4-hydroxymethylphosphinyl-2-butenoic acid (4.0 g, 18 mmol), (RuCl(p-cymene)((S)-binap)Cl (8.4 mg, 0.009 mmol), and methanol (20 ml) were added to a 200 ml autoclave, and a nitrogen substitution and a hydrogen substitution were performed. The temperature in the autoclave was set to 70° C., hydrogen gas was charged to 1 MPa, and the reaction solution was stirred at the same temperature for 5 hours. A part of the reaction solution was taken as a sample. After completion of the reaction was confirmed with high performance liquid chromatography (HPLC) analysis on the sample, reaction solution was cooled to room temperature, hydrogen was purged, and then the reaction solution was moved to a 100 ml flask. After methanol was removed in vacuo and water (20 ml) was added, the water phase was washed with toluene (10 ml) twice and 24.6 g of (S)-2-acetylamino-4-hydroxymethylphosphinylbutanoic acid was obtained as a solution. The optical purity of the obtained (S)-2-acetylamino-4-hydroxymethylphosphinylbutanoic acid was 90.8% ee.

Workup

  1. customwas set to 70° C.
  2. customAfter completion of the reaction was confirmed with high performance liquid chromatography (HPLC) analysis on the sample, reaction solution
  3. customhydrogen was purged
  4. customthe reaction solution was moved to a 100 ml flask
  5. customAfter methanol was removed in vacuo and water (20 ml)
  6. additionwas added
  7. washthe water phase was washed with toluene (10 ml) twice

Sources & evidence

ORD record
ord-c472b23da6fe4853b1a1def31e01e96c
Source dataset
uspto-grants-2011_12
Patent number
US08076503B2

Reaction notes

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