Hydrochloric Acid → HCID 59025479, compound

HRID 1444839Notes

Reaction equation

HRID 1444839 reaction equation
[Cl:1][C:2]1[CH:43]=[CH:42][C:5]2[CH:6]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:7](=[O:37])[N:8]([CH2:23][C:24]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]([O:34]CC)=[O:33])[CH2:28][CH2:27]3)=[O:25])[CH2:9][CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]#[C:18][Si](C)(C)C)[C:4]=2[CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CO.O>[Cl:1][C:2]1[CH:43]=[CH:42][C:5]2[CH:6]([CH2:38][CH:39]([CH3:40])[CH3:41])[C:7](=[O:37])[N:8]([CH2:23][C:24]([N:26]3[CH2:27][CH2:28][CH:29]([C:32]([OH:34])=[O:33])[CH2:30][CH2:31]3)=[O:25])[CH2:9][CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]#[CH:18])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59025505HCID 59025505, compound

Product 1

HCID 59025479HCID 59025479, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

12 mg of the compound from Example 31A (0.019 mol) are dissolved in 2.0 ml of THF/methanol (1:1), mixed with 100 μl of 1 N sodium hydroxide solution and stirred at room temperature for 16 h. The reaction solution is acidified with 1 N hydrochloric acid, diluted with water and extracted three times with dichloromethane. The combined organic phases are dried over sodium sulphate, and the residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 6 mg (58% 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. 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-9334ae18ff684ea585ad8752a0043661
Source dataset
uspto-grants-2010_02
Patent number
US07662956B2

Reaction notes

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