Sodium Hydroxide → HCID 22730348, compound

HRID 2356061Notes

Reaction equation

HRID 2356061 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([O:27]CC)=[O:26])=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)[O:11][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)[O:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22730175HCID 22730175, compound

Product 1

HCID 22730348HCID 22730348, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 186C (130 mg, 0.34 mmol) in THF (15.0 mL) and methanol (5.0 mL) at room temperature was treated with 2N sodium hydroxide (3.0 mL), stirred for 18 hours, concentrated, treated with water (2.0 mL), and adjusted to pH<7 with 2N HCl. The precipitate was filtered and dried under vacuum to provide the desired product. MS (DCI) m/e 356 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.72 (s, 1H), 8.18-8.15 (m, 2H), 8.08-8.04 (m, 4H), 7.97-7.86 (m, 4H), 7.31-7.28 (m, 2H), 2.35 (s, 3H).

Workup

  1. concentrationconcentrated
  2. additiontreated with water (2.0 mL)
  3. filtrationThe precipitate was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f57758508ea540b89f80297237a16dba
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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