Hydrochloric Acid → HCID 56932661, compound

HRID 574153Notes

Reaction equation

HRID 574153 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][CH:21]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=3)[C:22]([NH:24][C:25]3([C:28]([O:30]CC)=[O:29])[CH2:27][CH2:26]3)=[O:23])=[O:19])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].[OH-].[Na+].Cl>CO.CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][CH:21]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:40])([F:41])[F:42])[CH:34]=3)[C:22]([NH:24][C:25]3([C:28]([OH:30])=[O:29])[CH2:27][CH2:26]3)=[O:23])=[O:19])[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 66807332HCID 66807332, compound

Product 1

HCID 56932661HCID 56932661, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

64 mg (0.106 mmol) of the compound of Example 5 were dissolved in 3 ml of methanol, and 422 μl of a 1M aqueous lithium hydroxide solution (0.42 mmol) were added. The mixture was stirred at RT overnight. Since the reaction was very slow, another 210 μl (0.21 mmol) of a 1M sodium hydroxide solution were added and the mixture was stirred at RT for another 5 days. By addition of 1N hydrochloric acid, the mixture was adjusted to pH 2, diluted with a little DMSO and separated by preparative HPLC [Method 6]. This gave 37 mg (61% of theory) of the title compound.

Workup

  1. stirringthe mixture was stirred at RT for another 5 days
  2. customseparated by preparative HPLC [Method 6]

Sources & evidence

ORD record
ord-7146b84a88ec4c889f690e24a18a461c
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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