Sodium Hydroxide → HCID 178503036, compound

HRID 1525304Notes

Reaction equation

HRID 1525304 reaction equation
[F:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[N:12]=[C:11]([OH:13])[C:10]([C:14]([NH:16][C@@H:17]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:18]3[CH:23]=[CH:22][C:21]([P:24]([CH3:29])(=[O:28])[O:25]CC)=[CH:20][CH:19]=3)=[O:15])=[CH:9][N:8]=2)[CH:6]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[N:12]=[C:11]([OH:13])[C:10]([C:14]([NH:16][C@@H:17]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:18]3[CH:19]=[CH:20][C:21]([P:24]([CH3:29])(=[O:25])[OH:28])=[CH:22][CH:23]=3)=[O:15])=[CH:9][N:8]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178476766HCID 178476766, compound

Product 1

HCID 178503036HCID 178503036, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 28-h (3.8 g, 7.4 mmol) in 25 ml of dioxane was treated with 7.2 ml of 3N NaOH and heated at 80° C. for one hour. The mixture was cooled to room temperature and then 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 resulting solid was collected via filtration to give compound 28-1 (1.4 g of crude), which was further purified via prep-HPLC (150 mg, 4%). 1H NMR (300 MHz, CD3OD): δ 8.72 (s, 1H), 8.17 (s, 1H), 7.81 (m, 3H), 7.43 (m, 2H), 7.20 (m, 2H), 7.11 (m, 2H), 6.71 (s, 1H), 1.65 (d, 3H). (M+H)+=486.0.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. additionthe residue was diluted with water
  4. washwashed with ethyl acetate
  5. filtrationthe resulting solid was collected via filtration

Sources & evidence

ORD record
ord-949821a73db64b83a1fadae850d13648
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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