Hydrochloric Acid → HCID 57781000, compound

HRID 1011225Notes

Reaction equation

HRID 1011225 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:23][CH3:24])[C:11]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]1)[N:8]([CH2:25][C:26]([F:29])([F:28])[F:27])[CH:7]=[C:6]([C:30]([NH:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:36][C:35]=1[CH3:45])=[O:31])[C:5]2=[O:46].[OH-].[Li+].Cl>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:23][CH3:24])[C:11]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1)[N:8]([CH2:25][C:26]([F:29])([F:27])[F:28])[CH:7]=[C:6]([C:30]([NH:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][C:41]([F:42])([F:43])[F:44])=[CH:36][C:35]=1[CH3:45])=[O:31])[C:5]2=[O:46]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 87352825HCID 87352825, compound

Product 1

HCID 57781000HCID 57781000, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

550 mg (0.698 mmol) of the compound of Example 2 are provided in 10 ml of dioxane, 3.5 ml of a 1M solution of lithium hydroxide in water are added and the mixture is stirred overnight. The reaction mixture is acidified with 1N hydrochloric acid and freed from the solvents on a rotary evaporator. The residue is taken up in DMSO and separated by preparative chromatography (method 5). 330 mg (72% of theory) of the title compound are obtained.

Workup

  1. customfreed from the solvents on a rotary evaporator
  2. customseparated by preparative chromatography (method 5)

Sources & evidence

ORD record
ord-bc162e1f4f2843d08fa7de3c67a90064
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

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