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

HRID 81866

반응식

HRID 81866 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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.

출처 및 근거

ORD 기록
ord-c55bfc281ba74c569540eb90e8a3697a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846707B2

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