Ethylene Glycol → HCID 86705285, compound

HRID 705315Notes

Reaction equation

[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

Participants

Conditions

Temperature: 100 °C

Procedure

(+/−)-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.

Workup

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

Sources & evidence

ORD record: ord-bd36ec57d9c045a38d304ffdbf654fe7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173883B2

Reaction notes

Loading…