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Bpr-0L075 → tert-Butyl 5-((6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710367
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HRID 710367 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[O:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.CS(O[CH2:31][C:32]1([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][O:36][C:35]([CH3:39])([CH3:38])[O:34][CH2:33]1)(=O)=O>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12](=[O:13])[C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[CH:8][N:9]2[CH2:31][C:32]2([NH:40][C:41](=[O:42])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:37][O:36][C:35]([CH3:38])([CH3:39])[O:34][CH2:33]2)=[CH:5][CH:4]=1
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참가 물질

5

반응물 2

HCID 10359957Bpr-0L075HCID 86661783(5-(tert-Butoxycarbonylamino)-2,2-dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate

생성물 1

HCID 86661782tert-Butyl 5-((6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate수율 37.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매
HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of the product of Example 13, Step B (0.11 g; 0.32 mmol) in anhydrous DMF (0.6 ml) 60% NaH in mineral oil (0.02 g; 0.5 mmol) was added and the mixture was stirred for 1 h at room temperature under N2. To it, a product of Step A (0.13 g; 0.383 mmol) was added and the resulting mixture was stirred for 3 days at ˜55° C. under N2, cooled to room temperature and diluted to 15 ml with Et2O, washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2, CH2Cl2/EtOAc 8:2) to give the title compound (0.07 g; 37%) as a colourless solid. 1H-NMR (CDCl3) 1.23 (s, 9H); 1.46 (s, 3H); 1.53 (s, 3H); 3.71 (d, 2H, J=11.8 Hz); 3.84-3.94 (m, 15H); 4.12 (s, 1H); 4.76 (s, 2H); 6.96 (dd, 1H, J=2.2, 8.8 Hz); 7.06 (s, 2H); 7.16 (d, 1H, J=2.2 Hz); 7.44 (s, 1H); 8.24 (d, 1H, J=8.8 Hz).

후처리

  1. stirringthe resulting mixture was stirred for 3 days at ˜55° C. under N2
  2. temperaturecooled to room temperature
  3. washwashed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure
  7. customthe residue was purified by FCC (SiO2, CH2Cl2/EtOAc 8:2)

출처 및 근거

ORD 기록
ord-f3392a9969d341c2b07781da12961bfc
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181182B2

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