Acetic Acid → HCID 86612912, compound

HRID 915885Notes

Reaction equation

HRID 915885 reaction equation
[CH3:1][C@@:2]1([O:30]C(=O)C)[C@H:6]([O:7]C(=O)C)[C@@H:5]([CH2:11][O:12]C(=O)C)[O:4][C@H:3]1[N:16]1[CH:29]=[C:20]2[CH:21]=[CH:22][C:23]3[C:24](=[S:28])[NH:25][N:26]=[CH:27][C:18]([C:19]=32)=[N:17]1.[OH-].[Na+].C(O)(=O)C>C(O)C.O>[CH3:1][C@@:2]1([OH:30])[C@H:6]([OH:7])[C@@H:5]([CH2:11][OH:12])[O:4][C@H:3]1[N:16]1[CH:29]=[C:20]2[CH:21]=[CH:22][C:23]3[C:24](=[S:28])[NH:25][N:26]=[CH:27][C:18]([C:19]=32)=[N:17]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86612910HCID 86612910, compound

Product 1

HCID 86612912HCID 86612912, compoundYield 22.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of compound 23.1 (180 mg, 0.38 mmol) in 4 mL ethanol was added 0.22 mL of 1N sodium hydroxide solution in water. The mixture was stirred at room temperature for 1.5 hr. after which time the pH was brought to 6 with acetic acid and the solvent evaporated. The residue was purified on silica gel column (10:1 CH2Cl2:MeOH) to afford 30 mg of product 23.2. 1H NMR (DMSO-d6) δ 10.49 (s, 1H), 8.52 (s, 1H), 7.50 (s, 1H), 7.00 (d, J 12 Hz, 1H), 6.08 (s, 1H), 5.65 (d, J 12 Hz, 1H), 5.18 (m, 3H), 3.82 (m, 3H), 3.68 (m, 1H), 0.73 (s, 3H).

Workup

  1. customthe solvent evaporated
  2. customThe residue was purified on silica gel column (10:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-7b1059b824fa42468912578b7aeba4db
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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