Trimethyl phosphite → HCID 86726375, compound

HRID 629766Notes

Reaction equation

HRID 629766 reaction equation
Br[CH2:2][C:3]([N:5]1[C@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][O:7][C:6]1=[O:16])=[O:4].[P:17]([O:22]C)([O:20][CH3:21])[O:18][CH3:19]>C1(C)C=CC=CC=1>[O:4]=[C:3]([N:5]1[C@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][O:7][C:6]1=[O:16])[CH2:2][P:17](=[O:22])([O:20][CH3:21])[O:18][CH3:19]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 40562710HCID 40562710, compound

Product 1

HCID 86726375HCID 86726375, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (R)-3-(2-bromoacetyl)-4-phenyloxazolidin-2-one (175 g, 616 mmol) and trimethyl phosphite (83.3 g, 671 mmol) in toluene (870 mL) was heated to reflux for 16 h. The reaction mixture was cooled to ambient temperature and the solvent was concentrated under reduced pressure to give a brown colored gum, which was triturated with 1:1 CH2Cl2 and hexanes (250 mL) to provide a brown solid. The solid was collected by filtration under reduced pressure and washed with CH2Cl2 (50 mL) to provide the product (98.8 g) as light brown solid.

Workup

  1. temperatureto reflux for 16 h
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customto give a brown colored gum, which
  4. customwas triturated with 1:1 CH2Cl2 and hexanes (250 mL)
  5. customto provide a brown solid
  6. filtrationThe solid was collected by filtration under reduced pressure
  7. washwashed with CH2Cl2 (50 mL)

Sources & evidence

ORD record
ord-e31dbab713e9489f807b22cf956e4cd9
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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