Diethyl methylphosphonite → HCID 178476772, compound

HRID 2197454Notes

Reaction equation

HRID 2197454 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][N:7]1[C:15]([OH:16])=[N:14][C:13]2[C:8]1=[N:9][C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[N:11][C:12]=2[NH2:17].[CH2:26]([O:28][P:29]([CH3:33])[O:30]CC)[CH3:27]>O1CCOCC1>[NH2:17][C:12]1[N:11]=[C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])[N:9]=[C:8]2[C:13]=1[N:14]=[C:15]([OH:16])[N:7]2[CH2:6][C:5]1[CH:4]=[C:3]([CH2:2][P:29]([CH3:33])(=[O:30])[O:28][CH2:26][CH3:27])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 85063Diethyl methylphosphoniteHCID 178496187HCID 178496187, compound

Product 1

HCID 178476772HCID 178476772, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Compound (9) (0.148 mmol) and diethylmethylphosphonite (1 mL) in dioxane (2.5 mL) was placed in an oil bath preheated to 100° C. for 30 minutes. The progress of the reaction was monitored by LCMS at 10 minute intervals. Once the reaction was observed to be complete, all of the solvent and phosphonite reagent were evaporated under high vacuum, and the remaining product was purified by HPLC. Lyophylization of the crude product gave Compound (10) (8.9 mg, 14%) as a white powder. 1H NMR (300 MHz, CD3OD) δ 1.22 (t, J=6.9, 14.1 Hz, 2H), 1.36 (d, J=14.1 Hz, 3H), 3.20 (d, J=17.7 Hz, 2H), 3.38 (s, 3H), 3.69 (t, J=4.8, 9.6 Hz, 2H), 3.95 (m, 3H), 4.39 (t, J=4.8, 9.6 Hz, 2H), 4.97 (s, 2H), 7.24 (s, 1H), 7.31 (m, 3H). LCMS: m/z for C19H26N5O5P++H observed 436.1 at 1.29 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O (C18 column).

Workup

  1. waitThe progress of the reaction was monitored by LCMS at 10 minute
  2. customall of the solvent and phosphonite reagent were evaporated under high vacuum
  3. customthe remaining product was purified by HPLC

Sources & evidence

ORD record
ord-1ba51c9232f8460db470203aa65dca42
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

Loading…