반응 #675670

ord-2548cd4db9a44b65af484b2417b6e4f7

반응 방정식

C[C@@H](N)c1ccc(C(=O)OC(C)(C)C)s1.Cl
(R)-tert-butyl 5-(1-aminoethyl)thiophene-2-carboxylate hydrochloride
CCN(CC)CC
triethylamine
CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
O=C(O)c1cc2ccccc2s1
1-benzothiophene-2-carboxylic acid
C[C@@H](NC(=O)c1cc2ccccc2s1)c1ccc(C(=O)OC(C)(C)C)s1
(R)-tert-butyl 5-(1-(benzothiophene-2-carboxamido)ethyl)thiophene-2-carboxylate

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.STIRRINGThe mixture was stirred at rt for 16 h
  2. 2
    기타After separation
  3. 3
    추출the aqueous layer was extracted with DCM (2×3 mL)
  4. 4
    기타The combined organic phases were evaporated to dryness

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09227951B2uspto-grants-2016_01