Acetic Acid → HCID 10228407, compound

HRID 857368Notes

Reaction equation

HRID 857368 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH:5]1[C:9]2=[C:10]([S:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:11]3[C:12]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:13][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.[Li+].[OH-].CC(O)=O>C1COCC1.CO>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([S:25][C:10]2[C:11]3[C:12]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:13][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:15][C:16]=3[N:8]3[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:33])=[O:2])[C:9]=23)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 131726147HCID 131726147, compound

Product 1

HCID 10228407HCID 10228407, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the ester of Step 2 (70 mg) in THF/MeOH (3:1) mixture at r.t. was added 1 M LiOH aqueous solution (1 mL). The reaction mixture was stirred at r.t. for 1 hour. Then AcOH was added. The aqueous layer was extracted with EtOAC and the combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography, eluting with 1% AcOH in EtOAc to give 60 mg of the title compound.

Workup

  1. extractionThe aqueous layer was extracted with EtOAC
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 1% AcOH in EtOAc

Sources & evidence

ORD record
ord-d379636da4f547a9a6ed5f2cdf59a38f
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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