Dichloromethane → 2-{3-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl ester

HRID 1628173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628173
[Cl:1][C:2]([Cl:37])([Cl:36])[CH2:3][O:4][C:5](=[O:35])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]([O:23][CH2:24]C2C=CC(C(F)(F)F)=CC=2)=[O:22])[CH:15]=1.Cl[C:39](Cl)(Cl)COC(=O)C1C=CC=CC=1CSC1C=CC=C(CC(O)=O)C=1.[F:64][C:65]([F:76])([F:75])[C:66]1[CH:71]=[CH:70][C:69](C(O)C)=[CH:68][CH:67]=1.C(Cl)Cl>CN(C1C=CN=CC=1)C.CCCCCCC.CCOC(C)=O>[Cl:37][C:2]([Cl:1])([Cl:36])[CH2:3][O:4][C:5](=[O:35])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([C:21]([O:23][CH2:24][CH3:39])=[O:22])[C:69]2[CH:68]=[CH:67][C:66]([C:65]([F:64])([F:75])[F:76])=[CH:71][CH:70]=2)[CH:15]=1

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 1371861-[4-(Trifluoromethyl)phenyl]ethan-1-olHCID 668648212-(3-Carboxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl esterHCID 866503082-[3-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid 2,2,2-trichloro-ethyl ester

Produkt 1

HCID 866503112-{3-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl esterAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

The titled compound was prepared according to the method described for 2-[3-(4-trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid 2,2,2-trichloro-ethyl ester above from 2-(3-carboxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester (168 mg, 0.387 mmol), 1-(4-trifluoromethyl-phenyl)-ethanol (88 mg, 0.465 mmol), EDCxHCl (111 mg, 0.581 mmol), DMAP (4.7 mg, 0.039 mmol) and DCM (5 mL). The crude was submitted to flash chromatography using heptane and EtOAc (90/10) as eluent to yield the titled compound (157 mg, 67%) as an oil; 1H NMR (400 MHz, CDCl3): δ 1.52 (d, 3H), 3.59 (dd, 2H), 4.52 (s, 2H), 4.96 (s, 2H), 5.90 (m, 2H), 7.09-7.12 (m, 1H), 7.17-7.23 (m, 4H), 7.30-7.42 (m, 4H), 7.57 (d, 2H), 8.08 (d, 1H); Mass spectrum: M−H+ 604.

Aufarbeitung

  1. customThe titled compound was prepared

Quellen und Nachweise

ORD-Eintrag
ord-4c005492c11e433ebe5fe292f6d128b8
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785681B2

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