4-Methylmorpholine → 4-[4-(4-tert-Butoxycarbonylaminobutyl)phenylamino]butyric acid ethyl ester

HRID 1678293Notes

Reaction equation

HRID 1678293 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26]Br)[CH3:21].CN1CCOCC1>CN(C=O)C>[CH2:20]([O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26][NH:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:19])=[CH:17][CH:16]=1)[CH3:21]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 76300Ethyl 4-bromobutyrateHCID 11558019[4-(4-Aminophenyl)butyl]carbamic acid tert-butyl ester

Product 1

HCID 597505444-[4-(4-tert-Butoxycarbonylaminobutyl)phenylamino]butyric acid ethyl esterYield 18.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4-(4-aminophenyl)butyl]carbamic acid tert-butyl ester (1.7 g, 6.43 mmol), 4-bromo-n-butyric acid ethyl ester (1.88 g, 9.64 mmol), 4-methylmorpholine (1.0 mL, 9.64 mmol), and DMF (10 mL) was stirred at 85° C. for 3 hours under a nitrogen atmosphere. The solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 4:1, hexanes/ethyl acetate, v/v) to provide 27 (0.44 g, 18%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 1.23 (t, 3H), 1.47 (s, 9H), 1.55 (m, 4H), 1.96 (m, 2H), 2.43 (t, 2H), 2.51 (t, 2H), 3.19 (m, 4H), 4.14 (q, 2H), 6.54 (d, 2H), 7.00 (d, 2H). m/z (ESI) 379.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was purified by flash chromatography (silica gel, 4:1, hexanes/ethyl acetate, v/v)

Sources & evidence

ORD record
ord-538b7eb332864227a4429921d609b8ff
Source dataset
uspto-grants-2011_08
Patent number
US08008494B2

Reaction notes

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