Acetic Acid → HCID 10300251, compound

HRID 857401Notes

Reaction equation

HRID 857401 reaction equation
C[CH:2]([CH:6]1[C:10]2=[C:11]([C:20](=[O:30])[C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[C:28]#[N:29])[C:12]3[C:13]([Br:19])=[CH:14][C:15]([F:18])=[CH:16][C:17]=3[N:9]2[CH2:8][CH2:7]1)[C:3]([O-:5])=[O:4].C1C[O:34]CC1.CO.[Li+].[OH-].CC(O)=O>[Cl-].[Na+].O>[NH2:29][C:28]([C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:20]([C:11]1[C:12]2[C:13]([Br:19])=[CH:14][C:15]([F:18])=[CH:16][C:17]=2[N:9]2[CH2:8][CH2:7][CH:6]([CH2:2][C:3]([OH:5])=[O:4])[C:10]=12)=[O:30])=[O:34]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 131726151HCID 131726151, compound

Product 1

HCID 10300251HCID 10300251, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the compound of Step 1 (30 mg) in a 3/1 mixture of THF/MeOH (3 mL) was added 1N LiOH (1 mL, aqueous solution). The reaction mixture was stirred at r.t. for 16 h and AcOH (0.5 mL) and brine (5 mL) were added. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was swished in EtOAc to give 18 mg of the title compound as a white solid.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c77a1667023842afa4795e4a6dcbb54e
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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