2-(2,2,2-Trifluoro-N-Methylacetamido)Acetic Acid → Benzyl 2-(Benzyloxy)-4-(N-(4-Cyclohexylbenzyl)-2-(2,2,2-Trifluoro-N-Methylacetamido) Acetamido)Benzoate

HRID 81877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81877
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:39][C:40]([F:50])([F:49])[C:41]([N:43]([CH2:45][C:46](O)=[O:47])[CH3:44])=[O:42]>>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:31][CH:32]=2)[C:46](=[O:47])[CH2:45][N:43]([CH3:44])[C:41](=[O:42])[C:40]([F:49])([F:50])[F:39])[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 2619482-(2,2,2-Trifluoro-N-Methylacetamido)Acetic AcidHCID 68076486HCID 68076486, Verbindung

Produkt 1

HCID 86694679Benzyl 2-(Benzyloxy)-4-(N-(4-Cyclohexylbenzyl)-2-(2,2,2-Trifluoro-N-Methylacetamido) Acetamido)BenzoateAusbeute 97 %

Versuchsvorschrift

Secondary aniline 4 was coupled to carboxylic acid 44 on a 3.17 mmol scale via General Procedure B to furnish 45 (2.07 g, 97%): δH (400 MHz, CDCl3) 1.35-1.44 (m, 5H, [Cy] CH2), 1.71-1.90 (m, 6H, [Cy] CH2), 3.17 (s, 3H, CH3), 3.79 (s, 2H, CH2), 4.84 (s, 2H, CH2), 4.97 (s, 2H, CH2), 5.35 (s, 2H, CH2), 6.65 (s, 1H, CH), 6.78 (dd, J=8.4 and 1.6 Hz, 1H, CH), 7.10-7.19 (m, 4H, CH), 7.29-7.43 (m, 10H, CH), 7.86 (d, J=8.4 Hz, 1H, CH); δC (100 MHz, CDCl3) 25.8, 26.6, 34.2, 44.0, 51.2, 52.6, 66.7, 70.4, 77.2, 113.9, 115.0, 117.6, 119.8, 126.8, 126.9, 127.7, 128.0, 128.3, 128.3, 128.4, 128.6, 132.9, 133.6, 135.5, 135.6, 144.6, 147.5, 157.0, 158.4, 165.1, 165.4; LRMS (ES+) calcd for [C39H39F3N2O5+Na] 695.27. found 695.36.

Quellen und Nachweise

ORD-Eintrag
ord-cdd3c2e9c5c244dc8f868c358fdc1daa
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846707B2

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