Ethylene Glycol → HCID 86705285、化合物

HRID 705315ノート

反応式

HRID 705315 の反応式
[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

参加物

6

反応物 3

HCID 174Ethylene GlycolHCID 8000Boron trifluoride etherateHCID 86705286HCID 86705286、化合物

生成物 1

HCID 86705285HCID 86705285、化合物収率 100%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

(+/−)-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.

後処理

  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

出典と根拠

ORDレコード
ord-bd36ec57d9c045a38d304ffdbf654fe7
出典データセット
uspto-grants-2015_11
特許番号
US09173883B2

反応ノート

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