Ammonium Chloride → HCID 66759199, compound

HRID 880364Notes

Reaction equation

HRID 880364 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[CH:11]=[C:10]([O:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)[C:9]=1[C:31]1[O:35][N:34]=[C:33]([C:36]([NH:38][CH:39]2[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:40]2)=[O:37])[CH:32]=1.[Cl-].[NH4+]>O1CCOCC1.O.C(OCC)(=O)C.[Zn]>[C:48]([O:47][C:45]([N:42]1[CH2:41][CH2:40][CH:39]([NH:38][C:36]([C:33]2[CH:32]=[C:31]([C:9]3[C:10]([O:21][C:22]4[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=4)=[CH:11][C:12]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:13][C:8]=3[O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[O:35][N:34]=2)=[O:37])[CH2:44][CH2:43]1)=[O:46])([CH3:49])([CH3:50])[CH3:51]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 66759099HCID 66759099, compound

Product 1

HCID 66759199HCID 66759199, compoundYield 86.2%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 4-{[(5-{2,4-bis[(2-methoxyethoxy)methoxy]-6-(4-nitrophenoxy)phenyl}isoxazol-3-yl)carbonyl]amino}piperidine-1-carboxylate (5.3 g, 7.4 mmol) in a mixture of dioxane (100 mL) and water (20 mL) were added portion wise zinc powder (1 g, 14.8 mmol, 2 eq.) and ammonium chloride (3.9 g, 74 mmol, 10 eq.) at 100° C. After stirring for 30 minutes, the reaction mixture was cooled and diluted with ethyl acetate. After washing with 1 M Na2CO3 solution, the organic phase was dried over Na2SO4 and the solvent removed. The crude product was filtered over a small pad of silica gel eluting with hexane/ethyl acetate 3/1 to provide the title compound (4.38 g, 86% yield).

Workup

  1. temperaturethe reaction mixture was cooled
  2. washAfter washing with 1 M Na2CO3 solution
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customthe solvent removed
  5. filtrationThe crude product was filtered over a small pad of silica gel eluting with hexane/ethyl acetate 3/1

Sources & evidence

ORD record
ord-a9219c15197242d68c1ab5b0cb3397ca
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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