Potassium Carbonate → HCID 89814708、化合物

HRID 1496798ノート

反応式

HRID 1496798 の反応式
C(OC(C[N:7]1[C:16](=[O:17])[CH:15]2[CH:10]([CH:11]3[C:18](=[C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]2[C:13]([C:32]([OH:45])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:12]3)[C:8]1=[O:9])=O)C.[C:46]([O:52][CH2:53]Cl)(=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:45][C:32]([C:13]1[CH:14]2[C:18](=[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:11]([CH:12]=1)[CH:10]1[C:8]([N:7]([CH2:53][O:52][C:46](=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48])[C:16](=[O:17])[CH:15]21)=[O:9])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 89814504HCID 89814504、化合物

生成物 1

HCID 89814708HCID 89814708、化合物収率 48%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A similar procedure (Hursthouse, M. B.; Khan, A.; Marson, C. M.; Porter, R. A. Tetrahedron Lett 1995, 36, 33, 5979-5982) to that described for the preparation of 207 was followed using NRB (200 mg, 0.39 mmol) in dimethylformamide (2 mL), chloromethyl pivalate (41) (59 mg, 0.39 mmol) in dimethylformamide (0.5 mL), and potassium carbonate (54 mg, 0.39 mmol). Purification by flash chromatography (hexane/ethyl acetate 1:1) afforded 8 as a colourless solid (118 mg, 0.19 mmol, 48%). mp 95-98° C.; 1H NMR (400 MHz, CDCl3) δ 1.18-1.19 (8.4H, m, tBu), 1.25-1.26 (0.6H, m, tBu), 3.38 (0.2H, dd, J=7.9 and 4.5 Hz, W/H-3), 3.45 (0.5H, dd, J=7.9 and 4.5 Hz, Y/H-3), 3.51-3.59 (0.4H, m, 0.2H U/H-2 and U/H-3, 0.2H V/H-2), 3.63-3.64 (0.2H, m, W/H-4), 3.67-3.76 (0.9H, m, 0.2H V/H-3, 0.2H W/H-2 and 0.5H Y/H-2), 3.88-3.92 (0.3H, m, 0.1H U/H-1 and 0.2H V/H-1), 4.00-4.01 (0.5H, dt, J=4.5 and 1.3 Hz, Y/H-4), 4.20-4.21 (0.1H, m, U/H-4), 4.35-4.36 (0.2H, dt, J=4.5 and 1.3 Hz, V/H-4), 4.49-4.52 (0.7H, m, 0.2H W/H-1 and 0.5H Y/H-1), 5.26-5.29 (0.7H, m, CH2), 5.31-5.62 (3H, m, 1.3H CH2, 0.2H V/H-6, 0.5H Y/H-6 and 1H OH), 6.04-6.06 (0.3H, m, 0.1H U/H-6 and 0.211 W/H-6), 6.71-7.57 (16H, m, Ar), 8.42-8.50 (0.6H, m, 0.2H 2U/αPyr and 0.4H 2VαPyr), 8.54-8.55 (0.7H, m, 0.2H W/αPyr and 0.5H Y/αPyr), 8.61-8.63 (0.7H, m, 0.2H W/αPyr and 0.5H Y/αPyr); vmax(nujol)/cm−1 1140 and 1212 (C—O ester), 1586 (C═O imide), 1715 (C═O ester); m/z (FAB+) 626 (MH+, 67%), 120 (100); (Found: MH+ 626.2644, C39H36N3O5 requires 626.2655).

後処理

  1. customPurification by flash chromatography (hexane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-b39289bce3e147a4ac4aca85aaafb66c
出典データセット
uspto-grants-2015_12
特許番号
US09198420B2

反応ノート

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