Hydrochloric Acid → HCID 87160517, compound

HRID 574155Notes

Reaction equation

HRID 574155 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:35]3[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=3)[C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33]C)=[O:32])=[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:35]3[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:42])[F:43])[CH:36]=3)[C:26]([NH:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:27])=[O:23])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 87160525HCID 87160525, compound

Product 1

HCID 87160517HCID 87160517, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

78 mg (0.12 mmol) of the compound of Example 13 were dissolved in 2.3 ml of methanol, and 360 μl of a 1M aqueous lithium hydroxide solution (0.36 mmol) were added. The mixture was stirred at RT for 1 h 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 67 mg (88% of theory) of the title compound.

Workup

  1. customseparated by preparative HPLC [Method 6]

Sources & evidence

ORD record
ord-c93fca2ab7e9438d8a44cedf4538dd26
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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