Sodium Hydroxide → HCID 178503030, compound

HRID 1525299Notes

Reaction equation

HRID 1525299 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 178476760HCID 178476760, compound

Product 1

HCID 178503030HCID 178503030, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 27-e (0.90 g, 1.86 mmol) in 30 ml of dioxane was treated with 3 ml of 3N NaOH and heated at 80° C. for 2 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 resulting solids were collected via filtration to give 27-1 (400 mg 47.2%). 1H NMR (300 MHz, DMSO-d6): δ 10.06 (br, 1H), 8.62 (s, 1H), 8.38 (s, 1H), 8.07 (s, 1H), 7.70 (m, 2H), 7.39 (m, 2H), 6.73 (s, 1H), 4.88 (m, 1H), 1.52 (m, 9H), 1.16 (m, 5H). (M+H)+=456.2.

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. customresulting solids
  6. filtrationwere collected via filtration
  7. customto give 27-1 (400 mg 47.2%)

Sources & evidence

ORD record
ord-6a1ffd8fcffd48dcb8707b0397ce5282
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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