Ethylamine → HCID 66871077, compound
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]=1Participants
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 nm 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 nm 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-ce51e1ba11f94e2ca25534c21fade361
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815859B2
Reaction notes
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