Tert-Butylamine → 5-(2,2-Dimethyl-propyl)-isoxazole-3-carboxylic acid tert-butylamide
Reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[CH2:3][C:4]1[O:8][N:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[C:35]([NH2:39])([CH3:38])([CH3:37])[CH3:36]>C1COCC1.CC#N>[C:35]([NH:39][C:9]([C:6]1[CH:5]=[C:4]([CH2:3][C:2]([CH3:1])([CH3:13])[CH3:12])[O:8][N:7]=1)=[O:11])([CH3:38])([CH3:37])[CH3:36]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 5-(2,2-dimethyl-propyl)-isoxazole-3-carboxylic acid (125.4 g, 0.685 mol) in THF (1500 ml) and MeCN (1500 ml) is added HOBT (101.75 g, 0.753 mol) and EDCI (144.3 g, 0.753 mol). After stirred 30 min, tert-butyl amine (86.7 ml, 0.821 mol) is added dropwise under nitrogen atmosphere and then the reaction is stirred at rt for 1.5 h. The solvents are evaporated under reduced pressure and the residue is taken into DCM (2000 ml). The mixture is washed with saturated aq sodium bicarbonate (500 ml×2), the organic layer is dried over sodium sulfate and concentrated. The residue is purified by chromatography on silica (DCM) to give the product as white solid.
Workup
- stirringthe reaction is stirred at rt for 1.5 h
- customThe solvents are evaporated under reduced pressure
- washThe mixture is washed with saturated aq sodium bicarbonate (500 ml×2)
- dry with materialthe organic layer is dried over sodium sulfate
- concentrationconcentrated
- customThe residue is purified by chromatography on silica (DCM)
Sources & evidence
- ORD record
- ord-3262b5a95bf04b1faf4b1dd1a2e5f99a
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039455B2
Reaction notes
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