Hydrochloric Acid → HCID 59025530, compound

HRID 1444836Notes

Reaction equation

HRID 1444836 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]2[CH:6]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:7](=[O:35])[N:8]([CH2:21][C:22]([N:24]3[CH2:29][CH2:28][CH:27]([C:30]([O:32]CC)=[O:31])[CH2:26][CH2:25]3)=[O:23])[CH2:9][CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:12]=3[O:19][CH3:20])[C:4]=2[CH:3]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:41]=[CH:40][C:5]2[CH:6]([CH2:36][CH:37]([CH3:38])[CH3:39])[C:7](=[O:35])[N:8]([CH2:21][C:22]([N:24]3[CH2:25][CH2:26][CH:27]([C:30]([OH:32])=[O:31])[CH2:28][CH2:29]3)=[O:23])[CH2:9][CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:12]=3[O:19][CH3:20])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59025474HCID 59025474, compound

Product 1

HCID 59025530HCID 59025530, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

64 mg of the compound from Example 20 (0.11 mol) are dissolved in 3.3 ml of dioxane/water (2:1), mixed with 165 μl of 1 N sodium hydroxide solution and stirred at room temperature overnight. The reaction solution is acidified (pH 2) with 1 N hydrochloric acid and extracted three times with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated in a rotary evaporator, and the residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 61 mg (100% of theory) of the title compound are obtained.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated in a rotary evaporator
  4. customthe residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-0d44c4aeec004b15815b1a7eeb73077c
Source dataset
uspto-grants-2010_02
Patent number
US07662956B2

Reaction notes

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