Water → HCID 86694929, compound

HRID 2204694Notes

Reaction equation

HRID 2204694 reaction equation
[Br:1][C:2]1[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4](O)[CH:3]=1.[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[OH2:33]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:5]([C:6]([O:8][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:33])=[C:4]([O:22][CH2:19][C:2]2[CH:10]=[CH:9][CH:5]=[CH:4][CH:3]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66611704HCID 66611704, compound

Product 1

HCID 86694929HCID 86694929, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-2-hydroxy-5-(4-morpholinylmethyl)benzoic acid (may be prepared as described in Description 33; 302 mg, 0.96 mmol) in N,N-dimethylformamide (5 ml) was added potassium carbonate (396 mg, 2.87 mmol) and benzyl bromide (0.25 ml, 2.10 mmol). The mixture was stirred at room temperature for 72 hours. Water (10 ml) and ethyl acetate (20 ml) was added and the organic layer was separated, washed with water (3×10 ml), dried (MgSO4) and the solvent removed in vacuo. Purified by SP4 (20-50% ethyl acetate/hexane) to yield the title compound as an oil. 305 mg.

Workup

  1. customthe organic layer was separated
  2. washwashed with water (3×10 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customPurified by SP4 (20-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-435ea89c45804be498783d5adf90ba37
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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