HCID 178418361, compound → HCID 178475079, compound

HRID 658442Notes

Reaction equation

HRID 658442 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, compound3×HCID 178474814HCID 178474814, compound

Product 1

HCID 178475079HCID 178475079, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-2-acetylamino-4-hydroxymethylphosphinyl-2-butenoic acid (4.0 g, 18 mmol), (RuCl((R)-segphos)2(μ-Cl)3(Et2NH2) (0.150 g, 0.09 mmol), and methanol (40 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 HPLC analysis on the sample, reaction solution was cooled to room temperature, hydrogen was released, and then the reaction solution was moved to a 100 ml flask. After methanol was removed in vacuo and adding water (20 ml), the water phase was washed with toluene (10 ml) twice and a solution of (R)-2-acetylamino-4-hydroxymethylphosphinylbutanoic acid was obtained. The optical purity of the obtained (R)-2-acetylamino-4-hydroxymethylphosphinylbutanoic acid was 92.8% ee. Further, the conversion rate was 100%.

Workup

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

Sources & evidence

ORD record
ord-f18f897ab1b4476eada982ab3af4ba90
Source dataset
uspto-grants-2011_12
Patent number
US08076503B2

Reaction notes

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