Hydrochloric Acid → HCID 68008920、化合物

HRID 1429092ノート

反応式

HRID 1429092 の反応式
BrC1C=CC(S([O:11][C@@H:12]2[CH2:45][N:15]3[C:16](=[O:44])[C@@H:17]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][C@@H:25]4[CH2:30][C@@:26]4([C:31]([O:33][CH2:34][CH3:35])=[O:32])[NH:27][C:28](=[O:29])[C@@H:14]3[CH2:13]2)(=O)=O)=CC=1.[CH:46]1[C:59]2[C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[C:52](=[O:60])[NH:51][C:50]=2[CH:49]=[CH:48][CH:47]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>O.CS(C)=O>[C:40]([O:39][C:37]([NH:36][C@@H:17]1[C:16](=[O:44])[N:15]2[CH2:45][C@H:12]([O:60][C:52]3[N:51]=[C:50]4[C:59](=[C:58]5[C:53]=3[CH:54]=[CH:55][CH:56]=[CH:57]5)[CH:46]=[CH:47][CH:48]=[CH:49]4)[CH2:13][C@H:14]2[C:28](=[O:29])[NH:27][C@:26]2([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:30][C@H:25]2[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:38])([CH3:43])([CH3:42])[CH3:41].[C:40]([O:39][C:37]([NH:36][C@@H:17]1[C:16](=[O:44])[N:15]2[CH2:45][C@H:12]([O:11][C:46]3[C:59]4[C:50](=[N:51][CH:52]=[C:53]5[C:58]=4[CH:57]=[CH:56][CH:55]=[CH:54]5)[CH:49]=[CH:48][CH:47]=3)[CH2:13][C@H:14]2[C:28](=[O:29])[NH:27][C@:26]2([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:30][C@H:25]2[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:38])([CH3:43])([CH3:41])[CH3:42]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 18536(5H)-PhenanthridinoneHCID 10796Cesium carbonateHCID 86642249HCID 86642249、化合物

生成物 2

HCID 68008920HCID 68008920、化合物収率 120%HCID 68499992HCID 68499992、化合物

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

To (2S ,6S ,13aS,14aR,16aS,Z)-ethyl 2-(4-bromophenylsulfonyloxy)-6-(tert-butoxycarbonylamino)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (9.00 g, 12.6 mmol) and phenanthridin-6(5H)-one (3.08 g, 15.8 mmol) was added DMSO (50 ml). To this mixture was added cesium carbonate (6.17 g, 18.9 mmol) and the resulting mixture was heated at 75° C. for 3 hr. The reaction mixture was cooled to room temperature, diluted with water (400 ML) and neutralized with HCl (2N, 7.8 mL). The mixture was filtered and the white solid was rinsed with water. The solid was taken up in dichloromethane and filtered to remove insoluble phenanthridinone. The filtrate was concentrated and the residue was purified flash chromatography on silica gel (4:6 hexane/ethyl acetate) to provide the title compound (2R,6S,13aS,14aR,16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-5,16-dioxo-2-(phenanthridin yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo [1,2-a][1,4]diazacyclopentadecine-14a-carboxylate as a pale yellow solid (5.07g, 60% yield).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. washthe white solid was rinsed with water
  4. filtrationfiltered
  5. customto remove insoluble phenanthridinone
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified flash chromatography on silica gel (4:6 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-222efaad80464ada84dd154c0b8410b5
出典データセット
uspto-grants-2015_01
特許番号
US08937041B2

反応ノート

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