Sodium Hydroxide → HCID 178503029, compound

HRID 1525275Notes

Reaction equation

HRID 1525275 reaction equation
[OH:1][C:2]1[C:7]([C:8]([NH:10][C@@H: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]([N:30]2[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][C@@H: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]([N:30]2[CH:34]=[CH:33][CH:32]=[N:31]2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178476758HCID 178476758, compound

Product 1

HCID 178503029HCID 178503029, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-((S)-(4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamido)(phenyl)methyl)phenyl(methyl)phosphinate, 22-d, (2 g, 4.32 mmol) was dissolved in 7.2 ml of dioxane and treated with 7.2 ml of 3N NaOH. The mixture was heated at 80° C. for one hour. Then it was concentrated under vacuum and the residue was diluted with water and washed with ethyl acetate. The aqueous layer was acidified with conc. HCl to pH=1 and the expected product, 22-1, crashed out (1.4 g of crude). The product can be further purified via prep-HPLC. 1H NMR (300 MHz, DMSO-d6): δ 10.40 (br, 1H), 8.64 (s, 1H), 8.44 (s, 1H), 8.06 (s, 1H), 7.60 (m, 2H), 7.38 (m, 7H), 6.73 (s, 1H), 6.32 (d, 1H), 1.51 (d, 3H). (M−H)−=448.1.

Workup

  1. concentrationThen it was concentrated under vacuum
  2. additionthe residue was diluted with water
  3. washwashed with ethyl acetate
  4. customThe product can be further purified via prep-HPLC

Sources & evidence

ORD record
ord-a9553b3b506440bca8aa544889e30d05
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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