Triethylamine → HCID 67397401, compound
Reaction equation
C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH:34]=[C:33]1[C:41]([OH:43])=O.Cl.[NH2:45][C@@H:46]([C:48]1[S:52][C:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[CH:50][CH:49]=1)[CH3:47]>O.C(Cl)Cl>[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH:34]=[C:33]1[C:41]([NH:45][C@@H:46]([C:48]1[S:52][C:51]([C:53]([O:55][C:56]([CH3:57])([CH3:59])[CH3:58])=[O:54])=[CH:50][CH:49]=1)[CH3:47])=[O:43]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a 2-dram vial was added triethylamine (0.156 mL, 1.12 mmol), HATU (0.106 g, 0.28 mmol), 1-benzothiophene-2-carboxylic acid (0.050 g, 0.28 mmol), and DCM (3 mL). The solution was stirred at rt for 30 min, then transferred to another 2-dram vial containing solid (R)-tert-butyl 5-(1-aminoethyl)thiophene-2-carboxylate hydrochloride. The mixture was stirred at rt for 16 h. To the reaction was then added DCM (3 mL) and water (1 mL). After separation, the aqueous layer was extracted with DCM (2×3 mL). The combined organic phases were evaporated to dryness to give (R)-tert-butyl 5-(1-(benzothiophene-2-carboxamido)ethyl)thiophene-2-carboxylate as a brown solid. LC-MS: (FA) ES+ 388.
Workup
- stirringThe mixture was stirred at rt for 16 h
- customAfter separation
- extractionthe aqueous layer was extracted with DCM (2×3 mL)
- customThe combined organic phases were evaporated to dryness
Sources & evidence
- ORD record
- ord-2548cd4db9a44b65af484b2417b6e4f7
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227951B2
Reaction notes
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