Ammonium Chloride → 5-[2,4-bis(benzyloxy)-5-chlorophenyl]-4-amino-N-ethylisoxazole-3-carboxamide

HRID 389929Notes

Reaction equation

[CH2:1]([NH:3][C:4]([C:6]1[C:10]([N+:11]([O-])=O)=[C:9]([C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:16][C:15]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:8][N:7]=1)=[O:5])[CH3:2].[NH4+].[Cl-]>C1COCC1.O.[Zn]>[CH2:30]([O:29][C:15]1[CH:16]=[C:17]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]([Cl:20])=[CH:19][C:14]=1[C:9]1[O:8][N:7]=[C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])[C:10]=1[NH2:11])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-(2,4-bis-benzyloxy-5-chloro-phenyl)-4-nitro-isoxazole-3-carboxylic acid ethylamide (1 g, 1.97 mmol) in THF (7 ml) was added to a solution of NH4Cl (2.7 g, 50 mmol) in water (15 ml). Zinc dust (4 g, 61 mmol) was then added portion wise over 15 min with stirring at 0° C. After 30 min at 0° C., the mixture was filtered and the resulting cake was rinsed with MeOH. The combined filtrate were evaporated under vacuo to give 5-[2,4-bis(benzyloxy)-5-chlorophenyl]-4-amino-N-ethylisoxazole-3-carboxamide (820 mg, 82%).

Workup

filtrationthe mixture was filtered
washthe resulting cake was rinsed with MeOH
customThe combined filtrate were evaporated under vacuo

Sources & evidence

ORD record: ord-7aaa0072f0224065aa573549da319d11
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383616B2

Reaction notes

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