Sodium Hydroxide → HCID 178503038, compound

HRID 1525212Notes

Reaction equation

HRID 1525212 reaction equation
[OH:1][C:2]1[C:7]([C:8]([NH:10][CH:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]2[CH:17]=[CH:16][C:15]([P:18]([CH3:23])(=[O:22])[O:19]CC)=[CH:14][CH:13]=2)=[O:9])=[CH:6][N:5]=[C:4]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[N:3]=1.[OH-].[Na+]>O1CCOCC1>[OH:1][C:2]1[C:7]([C:8]([NH:10][CH:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]2[CH:13]=[CH:14][C:15]([P:18]([CH3:23])(=[O:19])[OH:22])=[CH:16][CH:17]=2)=[O:9])=[CH:6][N:5]=[C:4]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178476768HCID 178476768, compound

Product 1

HCID 178503038HCID 178503038, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The ethyl methylphosphinate 2-4 (130 mg, 0.27 mmol) was dissolved in 5 ml of dioxane and treated with 2 ml of 5N NaOH. The mixture was heated at reflux overnight. The mixture was then concentrated under vacuum and the residue was treated with 2 ml of trifluoroacetic acid. The mixture was re-evaporated and the residue was purified by prep-HPLC to provide the product, 2-5 (80 mg, 64%). 1H NMR (CD3OD, 300 MHz,): δ 8.76 (m, 2H), 8.48 (m, 2H), 8.01 (m, 1H), 7.77 (m, 2H), 7.61 (m, 1H), 7.51 (m, 2H), 7.29 (m, 5H), 6.39 (s, 1H), 1.61 (d, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was then concentrated under vacuum
  4. additionthe residue was treated with 2 ml of trifluoroacetic acid
  5. customThe mixture was re-evaporated
  6. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-99f1d9843afc4df38136f749c07bec65
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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