Hydrochloric Acid → HCID 56932611, compound

HRID 574152Notes

Reaction equation

HRID 574152 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][CH:25]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=3)[C:26]([NH:28][C:29]3([C:32]([O:34]CC)=[O:33])[CH2:31][CH2:30]3)=[O:27])=[O:23])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>CO.CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:16])([F:17])[F:18])[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][CH:25]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:44])[F:45])[CH:38]=3)[C:26]([NH:28][C:29]3([C:32]([OH:34])=[O:33])[CH2:31][CH2:30]3)=[O:27])=[O:23])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 56932561HCID 56932561, compound

Product 1

HCID 56932611HCID 56932611, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

78 mg (0.115 mmol) of the compound of Example 1 were dissolved in 2.2 ml of methanol, and 460 μl of a 1M aqueous lithium hydroxide solution (0.46 mmol) were added. The mixture was stirred at RT overnight and then adjusted to pH 2 by addition of 1N hydrochloric acid, diluted with a little DMSO and separated by preparative HPLC [Method 6]. This gave 64 mg (86% of theory) of the title compound.

Workup

  1. customseparated by preparative HPLC [Method 6]

Sources & evidence

ORD record
ord-f51f94c085494eb69a2361d7231933d1
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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