Acetonitrile → 4-[3-[6-(3-Bromo-5-dimethylaminomethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

HRID 416980Notes

Reaction equation

HRID 416980 reaction equation
[CH2:1]([O:3][C:4](=[O:42])[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]([CH2:28]OS(C)(=O)=O)[CH:25]=[C:24]([Br:34])[CH:23]=2)[C:10]=1[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:2].C1COCC1.[CH3:48]COC(C)=O.C[C:55]#[N:56]>CNC>[CH2:1]([O:3][C:4](=[O:42])[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]([CH2:28][N:56]([CH3:55])[CH3:48])[CH:25]=[C:24]([Br:34])[CH:23]=2)[C:10]=1[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 594968294-[3-[6-(3-Bromo-5-methanesulfonyloxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 594967924-[3-[6-(3-Bromo-5-dimethylaminomethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 674DimethylamineSolvent

Procedure

The a solution of 4-[3-[6-(3-Bromo-5-methanesulfonyloxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.5 g, 3.72 mmol) in MeCN (40 mL), N,N-dimethylamine 2M/THF (3.72 mL, 7.44 mmol) was added, and stirred at room temperature overnight. The solvent was removed under reduced pressure. Flash column chromatography (50% EtOAc/Hex) provided a light yellow oil (1.47 g, 64% yield). 1H NMR (CDCl3): δ 7.08 (t, 1H), 7.03 (s, 1H), 6.93 (s, 1H), 6.79 (s, 1H), 6.77 (d, 1H), 6.68 (d, 1H), 4.17-4.06 (m, 4H), 3.99 (dd, 2H), 3.92 (dd, 2H), 3.34 (s, 2H), 2.97 (dd, 2H), 2.63 (dd, 2H), 2.56-2.46 (m, 4H), 2.23 (s, 6H), 2.17-0.89 (m, 16H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c2037e0a609d405c8bde0050d4141745
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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