Sodium Hydroxide → HCID 178503031, compound

HRID 1525293Notes

Reaction equation

HRID 1525293 reaction equation
[CH:1]1([C@@H:7]([NH:20][C:21]([C:23]2[C:24]([OH:34])=[N:25][C:26]([N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)=[N:27][CH:28]=2)=[O:22])[C:8]2[CH:13]=[CH:12][C:11]([P:14]([CH3:19])(=[O:18])[O:15]CC)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>O1CCOCC1>[CH:1]1([C@@H:7]([NH:20][C:21]([C:23]2[C:24]([OH:34])=[N:25][C:26]([N:29]3[CH:33]=[CH:32][CH:31]=[N:30]3)=[N:27][CH:28]=2)=[O:22])[C:8]2[CH:13]=[CH:12][C:11]([P:14]([CH3:19])(=[O:15])[OH:18])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178476761HCID 178476761, compound

Product 1

HCID 178503031HCID 178503031, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 26-f (0.98 g, 2.03 mmol) in 15 ml of dioxane was treated with 2 ml of 5N NaOH and heated at 80° C. for 2 hour. The reaction solution 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 solids were collected via filtration to give 26-1 (170 mg 38.4%). 1H NMR (300 MHz, DMSO-d6): δ 10.06 (s, 1H), 8.60 (s, 1H), 8.37 (s, 1H), 8.04 (s, 1H), 7.70 (m, 2H), 7.50 (m, 2H), 6.70 (s, 1H), 4.87 (m, 1H), 1.52 (m, 9H), 1.15 (m, 5H). (M+H)+=456.1.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. additionthe residue was diluted with water
  4. washwashed with ethyl acetate
  5. filtrationthe resulting solids were collected via filtration
  6. customto give 26-1 (170 mg 38.4%)

Sources & evidence

ORD record
ord-0cf65df1e6a14d109e56f08cb00a9c4c
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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