Oxalyl chloride → Ethyl 2-[2-(tert-butoxycarbonylamino)ethylamino]-5-methylamino-thiazole-4-carboxylate
Reaction equation
FC(F)(F)/C=C/[C:5]([OH:7])=[O:6].[C:10](Cl)(=O)C(Cl)=O.Cl.Cl.[NH2:18][CH2:19][CH2:20][NH:21][C:22]1[S:23][C:24]([NH:32][CH3:33])=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:26]=1.CCOP(O)N([CH:42]([CH3:44])[CH3:43])C(C)C>ClCCl>[C:42]([O:7][C:5]([NH:18][CH2:19][CH2:20][NH:21][C:22]1[S:23][C:24]([NH:32][CH3:33])=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:26]=1)=[O:6])([CH3:44])([CH3:10])[CH3:43]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
(E)-4,4,4-Trifluorobut-2-enoic acid (25 mg, 0.18 mmol) was dissolved in dichloromethane (1 ml containing one drop of dimethyl formamide), oxalyl chloride was added (16 μl, 0.18 mmol) and the solution was stirred at room temperature for 10 minutes. This solution was added to a solution of ethyl 2-(2-aminoethylamino)-5-methylamino-thiazole-4-carboxylate dihydrochloride (48 mg, 0.15 mmol) and EDIPA (132 μl, 0.75 mmol) in anhydrous dichloromethane (1.5 ml) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile) to yield 30 mg of a solid (0.071 mmol, 47%).
Workup
- stirringthe resulting mixture was stirred at room temperature overnight
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile)
Sources & evidence
- ORD record
- ord-f07dd1a8c21e43fa84f5d1d735f2d5de
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321724B2
Reaction notes
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