4-Cyanobenzoic acid → benzyl 2-(benzyloxy)-4-(N-(4-(1-(4-cyanobenzoyl)piperidin-4-yl)benzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate

HRID 81866

Reaktionsgleichung

Reaktionsgleichung von HRID 81866
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([CH:48]3[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]3)=[CH:44][CH:43]=2)[C:26](=[O:40])[CH2:27][N:28]([CH3:39])[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[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.[C:54]([C:56]1[CH:64]=[CH:63][C:59]([C:60](O)=[O:61])=[CH:58][CH:57]=1)#[N:55]>>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41][C:42]2[CH:43]=[CH:44][C:45]([CH:48]3[CH2:49][CH2:50][N:51]([C:60](=[O:61])[C:59]4[CH:63]=[CH:64][C:56]([C:54]#[N:55])=[CH:57][CH:58]=4)[CH2:52][CH2:53]3)=[CH:46][CH:47]=2)[C:26](=[O:40])[CH2:27][N:28]([CH3:39])[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 120874-Cyanobenzoic acidHCID 68076260benzyl 2-(benzyloxy)-4-(2-(N,4-dimethylphenylsulfonamido)-N-(4-(piperidin-4-yl)benzyl)acetamido)benzoate

Produkt 1

HCID 89766028benzyl 2-(benzyloxy)-4-(N-(4-(1-(4-cyanobenzoyl)piperidin-4-yl)benzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoateAusbeute 89 %

Versuchsvorschrift

Condensation of 21 with 4-cyanobenzoic acid on a 0.10 mmol scale via General Procedure F furnished 24 (63 mg, 89%): δH (400 MHz, CDCl3) 1.59-1.72 (m, 4H, CH2), 1.83-1.94 (m, 2H, CH2), 2.39 (s, 3H, CH3), 2.79-3.21 (m, 8H, CH3, CH and CH2), 3.65 (s, 2H, CH2), 4.77 (s, 2H, CH2), 4.95 (s, 2H, CH2), 4.97 (s, 2H, CH2), 5.34 (s, 2H, CH2), 6.60 (t, J=8.4 Hz, 1H, CH), 6.69 (dd, J=8.0 and 1.6 Hz, 1H, CH), 7.03-7.12 (m, 4H, 4 CH (Ar)), 7.21-7.82 (m, 12H, 12 CH (Ar)); δC (100 MHz, CDCl3) 21.4, 29.5, 35.9, 42.0, 48.1, 51.3, 52.7, 66.9, 70.6, 113.3, 113.9, 119.9, 120.7, 126.7, 126.9, 127.3, 127.4, 127.9, 128.1 (2), 128.4, 128.5, 129.0, 129.4, 132.3, 132.9, 134.8, 135.0, 135.5, 135.6, 140.0, 143.3, 144.0, 144.8, 158.6, 165.2, 167.0, 168.3; LRMS (ES+) calcd for [C51H48N4O7S+H] 861.33 found 861.38.

Quellen und Nachweise

ORD-Eintrag
ord-c55bfc281ba74c569540eb90e8a3697a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846707B2

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