Lithium Hydroxide → HCID 21867471, compound

HRID 857332Notes

Reaction equation

HRID 857332 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[S:16]([CH3:18])=[O:17])[N:9]3[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][C:24]([O:26]CC)=[O:25])[C:8]=23)=[CH:4][CH:3]=1.C1COCC1.CO.[Li+].[OH-]>CC(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[S:16]([CH3:18])=[O:17])[N:9]3[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][C:24]([OH:26])=[O:25])[C:8]=23)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 90708541HCID 90708541, compound

Product 1

HCID 21867471HCID 21867471, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the ester of Step 13 (70 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/MeOH to give 35 mg of the desired acid 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-92f28287df894e0a8d54d6c25c634544
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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