Ammonium Chloride → 4-{3-[6-(3-Amino-5-benzo[1,3]dioxol-5-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester

HRID 420387Notes

Reaction equation

HRID 420387 reaction equation
[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[C:24]([C:31]3[CH:39]=[CH:38][C:34]4[O:35][CH2:36][O:37][C:33]=4[CH:32]=3)[CH:23]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:2].[Cl-].[NH4+]>[Zn]>[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:31]3[CH:39]=[CH:38][C:34]4[O:35][CH2:36][O:37][C:33]=4[CH:32]=3)[CH:25]=[C:26]([NH2:28])[CH:27]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:2]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 575864714-{3-[6-(3-Benzo[1,3]dioxol-5-yl-5-nitro-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester

Product 1

HCID 575864994-{3-[6-(3-Amino-5-benzo[1,3]dioxol-5-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl esterYield 87.2%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A similar procedure as described in Example 12, step 4 was used, starting from 4-{3-[6-(3-benzo[1,3]dioxol-5-yl-5-nitro-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (4.8 g, 7.38 mmol), zinc dust (2.46 g, 36.94 mmol), and ammonium chloride (3.95 g, 73.88 mmol) to obtain 4-{3-[6-(3-amino-5-benzo[1,3]dioxol-5-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (3.99 g, 87%) as a light yellow oil: ES(+)-HRMS m/e calculated for C36H45NO8 (M+H)+ 619.0000, found 619.0000.

Sources & evidence

ORD record
ord-7f179c55fc1540bbabbddf24e6f982c5
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

Loading…