Methanol → HCID 58958603, compound

HRID 915607Notes

Reaction equation

HRID 915607 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:13]([CH3:33])[C:14]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[N:17]=[C:16]([CH3:26])[C:15]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9].O.CO.[Li+].[OH-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:13]([CH3:33])[C:14]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[N:17]=[C:16]([CH3:26])[C:15]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:7]([CH:12]=1)[C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 58958620HCID 58958620, compound

Product 1

HCID 58958603HCID 58958603, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of step 1 (60 mg, 0.129 mmol) in a mixture of THF (4 mL), water (4 mL), and MeOH (2 mL), was added LiOH (32 mg, 1.32 mmol). The reaction mixture was vigorously stirred for 24 h, after which it was concentrated under reduced pressure, and diluted with water (10 mL). The solution was then acidified to pH ˜1 using 1 N HCl, and then extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was then purified by preparative HPLC to afford the title compound (32 mg, 58%) as a white solid. 1H NMR (400 MHz, acetone-d6) δ 2.12 (s, 3H), 2.23 (s, 3H), 2.9 (s, 3H), 3.74 (s, 3H), 6.87-6.90 (m, 2H), 6.92-6.98 (m, 1H), 7.03-7.11 (m, 1H), 7.16-7.27 (m, 4H), 7.30-7.36 (m, 2H), 7.40-7.45 (m, 2H); ES-MS m/z 428.3 (MH+); HPLC RT (min) 3.54.

Workup

  1. concentrationafter which it was concentrated under reduced pressure
  2. additiondiluted with water (10 mL)
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was then purified by preparative HPLC

Sources & evidence

ORD record
ord-77efa98da3534c9483d5b2c6a51ac632
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

Loading…