Ethylene Glycol → HCID 86705285, 화합물

HRID 879230노트

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HRID 879230 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C@H:18]1[CH2:23][C@@H:22]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:21](=[O:35])[C@@H:20]([CH3:36])[CH2:19]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:37](O)[CH2:38][OH:39].B(F)(F)F.CCOCC>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C@@H:18]1[CH2:19][C@H:20]([CH3:36])[C:21]2([O:39][CH2:38][CH2:37][O:35]2)[C@H:22]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 174Ethylene GlycolHCID 8000Boron trifluoride etherateHCID 86705286HCID 86705286, 화합물

생성물 1

HCID 86705285HCID 86705285, 화합물수율 100%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

(+/−)-Benzyl ((1R,3S,5R)-5-(3-((benzoxycarbonyl)amino) pyridin-4-yl)-3-methyl-2-oxocyclohexyl)carbamate (1.0 equiv.) was dissolved in dry THF (0.20 M) under nitrogen and ETHYLENE GLYCOL (8.0 equiv.) was added followed by BF3.OEt2 (1.4 equiv.). The solution was microwave vial and heated at 100° C. for 60 mins. The solution was diluted with EtOAc and washed with sat. sodium bicarbonate, water, brine, dried over sodium sulfate and concentrated. The crude material was purified by ISCO chromatography to afford (+/−)-benzyl ((6R,8R,10S)-8-(3-((benzoxycarbonyl)amino)pyridin-4-yl)-10-methyl-1,4-dioxaspiro[4.5]decan-6-yl)carbamate in 100% yield. LC/MS (m/z)=532.2 (MH+), Rt=0.81 min.

후처리

  1. washwashed with sat. sodium bicarbonate, water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude material was purified by ISCO chromatography

출처 및 근거

ORD 기록
ord-babc19e892364a7e90e6f641458f3e73
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987457B2

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