1,2-Dichloroethane → 3-(R)-(4-fluoro-phenyl)-3-(3-trifluoromethyl-benzenesulfonylamino)-N-(6-vinyl-1,2,3,4-tetrahydro-naphthalen-2-(R)-yl)-propionamide

HRID 32124

Reaktionsgleichung

Reaktionsgleichung von HRID 32124
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)(=[O:28])=[O:27])[CH2:9][C:10]([NH:12][C@@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:23]=O)[CH:19]=3)[CH2:14]2)=[O:11])=[CH:4][CH:3]=1.[CH:39](C1C=C2C(=CC=1)C[C@H](N)CC2)=C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:36])[F:37])[CH:30]=2)(=[O:27])=[O:28])[CH2:9][C:10]([NH:12][C@@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:23]=[CH2:39])[CH:19]=3)[CH2:14]2)=[O:11])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 68931519(6-vinyl-1,2,3,4-tetrahydro-naphthalen-2-(R)-yl)-amineHCID 865985073-(R)-(4-fluoro-phenyl)-N-(6-formyl-1, 2,3,4-tetrahydro-naphthalen-2-(R)-yl)-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide

Produkt 1

HCID 689267513-(R)-(4-fluoro-phenyl)-3-(3-trifluoromethyl-benzenesulfonylamino)-N-(6-vinyl-1,2,3,4-tetrahydro-naphthalen-2-(R)-yl)-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-(R)-(4-fluoro-phenyl)-N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-2-(R)-yl)-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide (391 mg, 1 mmol), crude (6-vinyl-1,2,3,4-tetrahydro-naphthalen-2-(R)-yl)-amine (190 mg, 1.1 mmol), HOBt (135 mg, 1 mmol) and EDC (191 mg, 1 mmol) in 2 mL of DMF was stirred overnight at RT. After quenching with Sat. NaHCO3 solution, the reaction mixture was extracted with EtOAc. The combined organic phase was washed brine, dried over Na2SO4, and evaporated in vacuo. Flash chromatography (SiO2, hexane/EtOAc=1:2) gave the desired compound as a white solid.

Aufarbeitung

  1. customAfter quenching with Sat. NaHCO3 solution
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washThe combined organic phase was washed brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c6fca46f016b47638702f04f3e807bba
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425631B2

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