Lithium Hydroxide → HCID 10298793, compound

HRID 857347Notes

Reaction equation

HRID 857347 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=[C:5]1[CH:15]([CH2:16][C:17]([O:19]C)=[O:18])[CH2:14][CH2:13][CH2:12][N:6]12.C1COCC1.CO.[Li+].[OH-]>CC(O)=O>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)=[C:5]1[CH:15]([CH2:16][C:17]([OH:19])=[O:18])[CH2:14][CH2:13][CH2:12][N:6]12

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 90871450HCID 90871450, compound

Product 1

HCID 10298793HCID 10298793, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the ester of Step 6 (45 mg) in a THF/MeOH (3:1) mixture at r.t. was added 1N LiOH (aqueous solution). The reaction mixture was stirred at r.t. for 2 h and AcOH was added. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated. The residue was swished in EtOAc to provide 20 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-88cb1e2bddf949ada84f3b129ce90724
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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