Sodium Hydroxide → HCID 22730348, compound

HRID 2085729Notes

Reaction equation

HRID 2085729 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) δ8.72 (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-91bc506af6564f318ddc5cc2a756708b
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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