Ammonia → {4-[4-(3-Carbamoylpropylamino)phenyl]butyl}carbamic acid tert-butyl ester

HRID 254377Notes

Reaction equation

C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:11][CH:10]=1)C.[NH3:28]>CO>[C:23]([O:22][C:20](=[O:21])[NH:19][CH2:18][CH2:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][CH2:7][CH2:6][CH2:5][C:4](=[O:3])[NH2:28])=[CH:10][CH:11]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 45 °C

Procedure

4-[4-(4-tert-Butoxycarbonylaminobutyl)phenylamino]butyric acid ethyl ester 420 (0.44 g, 1.16 mmol) was added to 7N NH3 in methanol (40 mL). The reaction was stirred at 30° C. for 18 hours, at 45° C. for 25 hours, and finally at 50° C. for 84 hours. The solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 20:1:0.1, chloroform/methanol/concentrated ammonium hydroxide, v/v) to provide 430 (0.23 g, 56%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.47 (s, 9H), 1.55 (m, 4H), 1.96 (m 2H), 2.37 (t, 2H), 2.50 (t, 2H), 3.11 (m, 4H), 6.52 (d, 2H), 6.97 (d, 2H). m/z (ESI) 350.

Workup

waitfinally at 50° C. for 84 hours
customThe solvent was evaporated in vacuo
customThe residue was purified by flash chromatography (silica gel, 20:1:0.1, chloroform/methanol/concentrated ammonium hydroxide, v/v)

Sources & evidence

ORD record: ord-488a1a10ac924dc3859db0752f81fae5
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875619B2

Reaction notes

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