Hydrochloric Acid → HCID 68008920, 화합물

HRID 1429092노트

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HRID 1429092 반응식
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]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 18536(5H)-PhenanthridinoneHCID 10796Cesium carbonateHCID 86642249HCID 86642249, 화합물

생성물 2

HCID 68008920HCID 68008920, 화합물수율 120%HCID 68499992HCID 68499992, 화합물

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
75 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-222efaad80464ada84dd154c0b8410b5
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937041B2

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