Chlorosuccinimide → HCID 86622735, compound

HRID 2410368Notes

Reaction equation

HRID 2410368 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[O:7][C:8]1[C:13]2[C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[N:15][O:16][C:12]=2[CH:11]=[CH:10][CH:9]=1.C(=O)(O)[O-].[Na+].ClN1C(=O)CCC1=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[O:7][C:8]1[C:13]2[C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[N:15][O:16][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 69317858HCID 69317858, compound

Product 1

HCID 86622735HCID 86622735, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 4-{[(4-{[trans-2-hydroxycyclopentyl]oxy}-1,2-benzisoxazole-3-yl)oxy]-methyl}piperidine-1-carboxylate (158 mg, 0.365 mmol, EXAMPLE 32, step 1), 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO, 2.4 mg, 0.015 mmol), sodium bicarbonate (98.3 mg, 1.17 mmol), and tetra-n-butylammonium bromide (8.2 mg, 0.025 mmol) in dichloromethane (2 mL) and water (0.4 mL) was added N-chlorosuccinimide (60.3 mg, 0.453 mmol) at ambient temperature. After being stirred for 4 h, the mixture was quenched with aq. sodium thiosulfate. The mixture was extracted with ethyl acetate (20 mL) and washed with aq. potassium carbonate and brine. The extract was dried over magnesium sulfate and concentrated in vacuo to give 167 mg (crude mixture) of the title compound.

Workup

  1. customthe mixture was quenched with aq. sodium thiosulfate
  2. extractionThe mixture was extracted with ethyl acetate (20 mL)
  3. washwashed with aq. potassium carbonate and brine
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-170cb6697cb94432bec33cbe214be067
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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