Hydrochloric Acid → 4-[4-(4-Aminobutyl)phenylamino]butyric acid

HRID 254379Notes

Reaction equation

[OH-].[Na+].C([O:5][C:6](=[O:29])[CH2:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21]C(OC(C)(C)C)=O)=[CH:13][CH:12]=1)C.Cl>O.C1COCC1>[NH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][CH2:9][CH2:8][CH2:7][C:6]([OH:29])=[O:5])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.5N aqueous NaOH (1.2 mL) was added to a solution of 4-[4-(4-tert-butoxycarbonylaminobutyl)phenylamino]butyric acid ethyl ester 420 (0.45 g, 1.18 mmol) dissolved in a mixture of water (25 mL) and THF (30 mL). The reaction was stirred for 2 h. 12 N HCl was added dropwise until pH 3. The solvent was evaporated in vacuo. The residue was cooled to 0° C. and a solution of TFA/dichloromethane (10 mL) was added. The reaction was stirred for 30 minutes. The solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 4:1:0.1, chloroform/methanol/concentrated ammonium hydroxide, v/v) to provide 460 (0.38 g, 100%). 1H NMR (300 MHz, CD3OD) δ 1.61 (m, 4H), 1.82 (m, 2H), 2.29 (t, 2H), 2.50 (m, 2H), 2.88 (m, 2H), 3.09 (t, 2H), 6.58 (d, 2H), 6.92 (d, 2H). m/z (ESI) 251.

Workup

customThe solvent was evaporated in vacuo
additiona solution of TFA/dichloromethane (10 mL) was added
stirringThe reaction was stirred for 30 minutes
customThe solvent was evaporated in vacuo
customThe residue was purified by flash chromatography (silica gel, 4:1:0.1, chloroform/methanol/concentrated ammonium hydroxide, v/v)

Sources & evidence

ORD record: ord-361b892ed5b04a9a9397dc7378e65b3a
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875619B2

Reaction notes

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