Ethylamine → HCID 66871077, compound

HRID 589566Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:21]1CCO[CH2:23][CH2:22]1.ClC(OCC(C)C)=O.C(N)C>O1CCCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]([NH:21][CH2:22][CH3:23])=[O:12])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: -25 °C

Procedure

To 1.1 g (3.85 mM) of [(tert-butoxycarbonyl)amino](4-chlorophenyl)acetic acid in 10 ml of tetrahydrofurane were added, under stirring at −25° C., 0.5 ml (4.6 mM) of 4-methyl morpholine and 0.52 ml (4.0 mM) of isobutyl chloroformate. After 10 mn were then added, at −25° C. under stirring, 1.9 ml (3.85 mM) of ethylamine 2M in tetrahydrofurane. The reaction mixture was stirred at −25° C. for 1 h, and at room temperature for 16 h. The reaction mixture was filtered and the filtrate was concentrated under vacuum to give an oil, which was further purified by silica gel column chromatography, using dichloromethane/cyclohexane (75/25) as eluant, to give 520 mg of tert-butyl 1-(4-chlorophenyl)-2-(ethylamino)-2-oxoethylcarbamate as a white solid.

Workup

additionAfter 10 mn were then added, at −25° C.
stirringunder stirring
stirringThe reaction mixture was stirred at −25° C. for 1 h
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under vacuum
customto give an oil, which
customwas further purified by silica gel column chromatography

Sources & evidence

ORD record: ord-3f6dbcc915974f35bdee4cf63a2a0070
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233937B2

Reaction notes

Loading…