Triphenylphosphine → (R)-2-(2,4,6-Trichloro-pyrimidin-5-yloxy)-propionic acid ethyl ester

HRID 528452Notes

Reaction equation

HRID 528452 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[N:3]=1.[CH2:11]([O:13][C:14](=[O:18])[C@H:15](O)[CH3:16])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[CH2:11]([O:13][C:14](=[O:18])[C@H:15]([O:9][C:5]1[C:4]([Cl:10])=[N:3][C:2]([Cl:1])=[N:7][C:6]=1[Cl:8])[CH3:16])[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 637513ethyl (2R)-2-hydroxypropanoateHCID 5363146Diisopropyl azodicarboxylateHCID 866673322,4,6-Trichloropyrimidin-5-ol

Product 1

HCID 86711739(R)-2-(2,4,6-Trichloro-pyrimidin-5-yloxy)-propionic acid ethyl esterYield 57.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,4,6-trichloro-pyrimidin-5-ol (600 mg, 3.01 mmol), (R)-2-hydroxy-propionic acid ethyl ester (411 μL, 3.60 mmol), triphenylphosphine (906 mg, 3.45 mmol) and DIAD (678 μL, 3.45 mmol) in dioxane (5 mL) was stirred at RT for 18 hours before being concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0-25% ethyl acetate in cyclohexane) affording (R)-2-(2,4,6-Trichloro-pyrimidin-5-yloxy)-propionic acid ethyl ester (522 mg, 52%). 1H NMR (400 MHz, CDCl3): δ 4.30-4.16 (2H, m), 4.12 (1H, q, J=7.14 Hz), 1.70 (3H, d, J=6.78 Hz), 1.29 (3H, t, J=7.19 Hz).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, gradient 0-25% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-4b434db0af1f41368810c66522e7fa17
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

Loading…