Sodium Hydroxide → HCID 178503040, compound

HRID 574658Notes

Reaction equation

HRID 574658 reaction equation
[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:34])=[N:19][C:20]([N:23]2[CH:27]=[C:26]([P:28]([CH3:33])(=[O:32])[O:29]CC)[CH:25]=[N:24]2)=[N:21][CH:22]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1.O>[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:34])=[N:19][C:20]([N:23]2[CH:27]=[C:26]([P:28]([CH3:33])(=[O:29])[OH:32])[CH:25]=[N:24]2)=[N:21][CH:22]=1)=[O:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178476771HCID 178476771, compound

Product 1

HCID 178503040HCID 178503040, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

The product of step D, 1-1-d, (500 mg, 1.05 mmol) was dissolved in 10 mL of dioxane and treated with 2 mL of 5N NaOH. The mixture was heated at 80° C. for 30 min. The mixture was then diluted with water and extracted with dichloromethane. The aqueous layer was adjusted to pH=5 with AcOH and evaporated to dryness. The residue was used for prep-HPLC to afford the product, 1-1, (130 mg, 28%). 1H NMR (300 MHz, DMSO-d6): δ 10.38 (br, 1H), 8.79 (s, 1H), 8.48 (s, 1H), 8.18 (s, 1H), 7.37 (m, 10H), 6.29 (d, 1H), 1.63 (d, 3H). (M+H)+ =450.1.

Workup

  1. extractionextracted with dichloromethane
  2. customevaporated to dryness
  3. customto afford the product, 1-1, (130 mg, 28%)

Sources & evidence

ORD record
ord-32483f63a3e24e5493779d5f165c9e06
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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