Acetic Acid → HCID 16063374, compound

HRID 641711Notes

Reaction equation

HRID 641711 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:32])[CH:12]2[CH2:31][N:16]3[C:17]4[C:22]([C:23](/[CH:24]=[CH:25]/[C:26]([O:28]CC)=[O:27])=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].CC(O)=O>C1COCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:32])[CH:12]2[CH2:31][N:16]3[C:17]4[C:22]([C:23](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86636091HCID 86636091, compound

Product 1

HCID 16063374HCID 16063374, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 85 mg of the product from Step 2 in 2 mL of THF and 3 mL of MeOH was added 0.5 mL of 2N NaOH. The mixture was heated at 50° C. for 8 h and 1 mL of AcOH was then added, and concentrated. The residue was suspended in 5 mL of water and the solid was collected by filtration, and then purified by Combiflash eluted with a gradient up to 70% EtOAc/hexane containing 5% of AcOH to give 9 mg of the title compound (eluted first). 1H NMR (500 MHz, acetone-d6) d 8.12 (m, 2H), 7.87 (d, 1H), 7.87 (m, 1H), 7.48 (t, 1H), 7.42 (m, 1H), 7.28 (m, 2H), 6.28 (d, 1H), 4.65 (m, 1H), 4.27 (m, 1H), 4.04 (t, 1H), 3.49 (m, 1H), 3.10 (m, 1H), 3.02 (s, 3H), 2.10 (m, 1H), 1.78 (m, 1H).

Workup

  1. concentrationconcentrated
  2. filtrationthe solid was collected by filtration
  3. custompurified by Combiflash
  4. washeluted with a gradient up to 70% EtOAc/hexane containing 5% of AcOH

Sources & evidence

ORD record
ord-9e5aceccbc45499498b7d3b2dc678b84
Source dataset
uspto-grants-2010_04
Patent number
US07696222B2

Reaction notes

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