Sodium Hydroxide → HCID 68953819, compound

HRID 1887471Notes

Reaction equation

HRID 1887471 reaction equation
[OH:1][C:2]1[C:3]([O:30][CH3:31])=[CH:4][C:5]2[CH2:14][CH2:13][N:12]3[CH:7]([CH2:8][C:9]4[C:18]([Cl:19])=[CH:17][C:16]([O:20][CH3:21])=[C:15]([O:22][CH2:23][C:24]([O:26]CC)=[O:25])[C:10]=4[CH2:11]3)[C:6]=2[CH:29]=1.[OH-].[Na+]>C(O)C>[OH:1][C:2]1[C:3]([O:30][CH3:31])=[CH:4][C:5]2[CH2:14][CH2:13][N:12]3[CH:7]([CH2:8][C:9]4[C:18]([Cl:19])=[CH:17][C:16]([O:20][CH3:21])=[C:15]([O:22][CH2:23][C:24]([OH:26])=[O:25])[C:10]=4[CH2:11]3)[C:6]=2[CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68948964HCID 68948964, compound

Product 1

HCID 68953819HCID 68953819, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A product obtained in Example 55 (3.1 g, 6.9 mmol) was dissolved in ethanol (50 ml), adding 1 mol/L NaOH (13.9 ml). The mixture was stirred at room temperature for 2 hours. Then the mixture was concentrated under reduced pressure followed by adding water. The aqueous phase was washed with ethyl acetate and adjust to pH 5˜6 by 1 mol/L hydrochloric acid. The precipitated solid was collected by filtration and washed by water to give pale yellow powder. The solid was dissolved in alkali solution and adjust the pH again to give the refine product (2.6 g, 89.5%). mp 172˜174° C. 1HNMR (DMSO-d6) δ: 2.30˜2.49 (2H, m, CH2), 2.58˜2.63 (1H, d, CH2), 2.89˜2.95 (1H, m, CH2), 3.08 (1H, dd, CH2), 3.23 (1H, dd, N—CH), 3.38˜3.47 (2H, m, CH2), 3.74 (3H, s, Ar—OCH3), 3.79 (1H, s, Ar—OCH3), 4.25 (1H, d, CH2), 4.59 (2H, q, OCH2CO), 6.66 (1H, s, ArH), 6.73 (1H, s, ArH), 7.05 (1H, s, ArH).

Workup

  1. concentrationThen the mixture was concentrated under reduced pressure
  2. additionby adding water
  3. washThe aqueous phase was washed with ethyl acetate
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed by water
  6. customto give pale yellow powder
  7. dissolutionThe solid was dissolved in alkali solution

Sources & evidence

ORD record
ord-252f345319f74ca1bc4b5165ad4f0adc
Source dataset
uspto-grants-2013_08
Patent number
US08501762B2

Reaction notes

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