Triethylamine → N1-(4-(2-aminocyclopropyl)phenyl)-N8-hydroxyoctanediamide hydrochloride
Reaction equation
[Cl:1]C(OCC)=O.C(N(CC)CC)C.C(OC([NH:21][CH:22]1[CH2:24][CH:23]1[C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:42])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39](O)=[O:40])=[CH:27][CH:26]=1)=O)(C)(C)C.COC([O:48][NH2:49])(C)C>O1CCCC1>[ClH:1].[NH2:21][CH:22]1[CH2:24][CH:23]1[C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:42])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([NH:49][OH:48])=[O:40])=[CH:27][CH:26]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl chloroformate (0.384 mmol, 0.04 mL) and triethylamine (0.42 mmol, 0.06 mL) were added to a cooled (0° C.) solution of 8-(4-(2-tert-butoxycarbonylaminocyclopropyl)phenylamino)-8-oxooctanoic acid (0.32 mmol, 130 mg) in dry tetrahydrofuran (5 mL), and the mixture was stirred for 10 min. The solid was filtered off, and O-(2-methoxy-2-propyl)hydroxylamine (0.96 mmol, 0.7 mL) was added to the filtrate. The solution was stirred for 15 min at 0° C., then a 6 N HC1 solution (10 mL) was added, and the stirring was continued for further 12 h. Therefore the precipitate was filtered and washed with diethyl ether (3×10 mL) to give the pure N1-(4-(2-aminocyclopropyl)phenyl)-N8-hydroxyoctanediamide hydrochloride (9).
Workup
- filtrationThe solid was filtered off
- stirringThe solution was stirred for 15 min at 0° C.
- waitthe stirring was continued for further 12 h
- filtrationTherefore the precipitate was filtered
- washwashed with diethyl ether (3×10 mL)
Sources & evidence
- ORD record
- ord-7753f06cfae04a8b8f81b7fd91d09898
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765820B2
Reaction notes
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