Hydrochloric Acid → {2-[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]ethylamino}acetic acid

HRID 1509865Notes

Reaction equation

HRID 1509865 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][NH:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:12][CH:11]=1)C.[Li+].[OH-].Cl>C1COCC1>[C:24]([O:23][C:21]([NH:20][CH2:19][CH2:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][NH:6][CH2:5][C:4]([OH:28])=[O:3])=[CH:11][CH:12]=1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58809798{2-[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]ethylamino}acetic acid ethyl ester

Product 1

HCID 58809800{2-[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]ethylamino}acetic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 2 (0.28 g, 0.71 mmol) dissolved in THF (5 mL) was treated with LiOH (89 mg, 2.13 mmol, dissolved in 2 mL water) at room temperature overnight. The reaction mixture was neutralized with 2 N HCl aqueous solution to pH 5, and concentrated under vacuum. The resulting residue was co-evaporated with ethanol twice, and then loaded onto silica gel in a column. The product was eluted with a mixture of methanol (0-22%), ammonium hydroxide (0-2.2%) and dichloromethane (100-75.8%) to afford the desired product 11 (0.25 g, 96% yield) as a white solid. 1H NMR (500 MHz, CD3OD) δ 1.42 (s, 9H), 1.48 (m, 2H), 1.62 (m, 2H), 2.58 (t, 2H), 3.06 (m, 2H), 3.45 (m, 2H), 3.70 (s, 2H), 4.26 (m, 2H), 6.90 (d, 2H), 7.16 (d, 2H). m/z (ESI) 367.

Workup

  1. concentrationconcentrated under vacuum
  2. washThe product was eluted with a mixture of methanol (0-22%), ammonium hydroxide (0-2.2%) and dichloromethane (100-75.8%)

Sources & evidence

ORD record
ord-cd006ab3b9e948169493b131df783d93
Source dataset
uspto-grants-2012_07
Patent number
US08211895B2

Reaction notes

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