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Cesium carbonate → HCID 131736377, 화합물

HRID 1055482
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HRID 1055482 반응식
[CH3:1][N:2]([C@@H:10]([CH3:31])[C:11](=[O:30])[NH:12][CH:13]1[C:19]2([CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[O:18][C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[NH:15][C:14]1=[O:29])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].CS(O[CH2:37][C:38]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][C:39]=1[O:48][CH:49]([F:51])[F:50])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[F:50][CH:49]([F:51])[O:48][C:39]1[CH:40]=[CH:41][C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:38]=1[CH2:37][N:15]1[C:14](=[O:29])[C@@H:13]([NH:12][C:11](=[O:30])[C@@H:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7])[CH3:31])[C:19]2([CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[O:18][C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]1=2.[F:50][CH:49]([F:51])[O:48][C:39]1[CH:40]=[CH:41][C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:38]=1[CH2:37][N:15]1[C:14](=[O:29])[C@H:13]([NH:12][C:11](=[O:30])[C@@H:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7])[CH3:31])[C:19]2([CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[O:18][C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]1=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 90037025HCID 90037025, 화합물HCID 118574082HCID 118574082, 화합물

생성물 2

HCID 131736376HCID 131736376, 화합물수율 30%HCID 131736377HCID 131736377, 화합물수율 42%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

A mixture of tert-butyl methyl((2S)-1-oxo-1-(4-oxo-2′,3′,4,5,5′,6′-hexahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-3-ylamino)propan-2-yl)carbamate (118 mg, 272 μmol), (2-(difluoromethoxy)naphthalen-1-yl)methyl methanesulfonate (98.7 mg, 327 μmol) and Cs2CO3 (115 mg, 354 μmol) in DMF (681 μL) was stirred at RT for 20 h. The mixture was diluted with EtOAc, washed with H2O and brine, then dried over Na2SO4, and filtered. The filtrate was concentrated to give a residue that was purified by silica gel chromatography. The resulting material was purified by SFC to provide tert-butyl (S)-1-((S)-5-((2-(difluoromethoxy)naphthalen-1-yl)methyl)-4-oxo-2′,3′,4,5,5′,6′-hexahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (52.6 mg, 30%) as a white foam (MS m/z 662 (MNa)′) and tert-butyl (S)-1-((R)-5-((2-(difluoromethoxy)naphthalen-1-yl)methyl)-4-oxo-2′,3′,4,5,5′,6′-hexahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (72.8 mg, 42%) as a white foam (MS m/z 662 (MNa)+).

후처리

  1. washwashed with H2O and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customto give a residue that
  6. customwas purified by silica gel chromatography
  7. customThe resulting material was purified by SFC

출처 및 근거

ORD 기록
ord-4ea00d6d93ec4775949ff184513edaaf
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394263B2

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