Sulfuric acid tetrahydrofuran → HCID 178487603, compound

HRID 2202325Notes

Reaction equation

HRID 2202325 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].C1COCC1.[F:11][C:12]1[CH:13]=[C:14]([NH:23][C:24]([C@@H:26]2[N:35]([C:36]([C@@H:38]3[CH2:41][C@H:40]([CH2:42][C:43]([OH:45])=[O:44])[CH2:39]3)=[O:37])[CH2:34][CH2:33][C:32]3[N:31]=[C:30]([O:46][CH3:47])[CH:29]=[CH:28][C:27]2=3)=[O:25])[CH:15]=[C:16]2[C:20]=1[C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17]2>C1COCC1>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[F:11][C:12]1[CH:13]=[C:14]([NH:23][C:24]([C@@H:26]2[N:35]([C:36]([C@@H:38]3[CH2:41][C@H:40]([CH2:42][C:43]([OH:45])=[O:44])[CH2:39]3)=[O:37])[CH2:34][CH2:33][C:32]3[N:31]=[C:30]([O:46][CH3:47])[CH:29]=[CH:28][C:27]2=3)=[O:25])[CH:15]=[C:16]2[C:20]=1[C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17]2

Participants

4

Reactant 2

HCID 68124251Sulfuric acid tetrahydrofuranHCID 178487600HCID 178487600, compound

Product 1

HCID 178487603HCID 178487603, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.126M Sulfuric acid/THF (13.24 mL, 1.67 mmol) solution was added to a solution of (cis-3-(((5R)-5-((7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)carbamoyl)-2-methoxy-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)carbonyl)cyclobutyl)acetic acid (850 mg, 1.67 mmol) in THF (20 mL) at room temperature. The mixture was concentrated under reduced pressure to dryness, and the solid was collected by filtration with ethyl acetate (20 mL) to give (cis-3-(((5R)-5-((7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)carbamoyl)-2-methoxy-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)carbonyl)cyclobutyl)acetic acid monosulfate (980.1 mg, 1.613 mmol, 97%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure to dryness
  2. filtrationthe solid was collected by filtration with ethyl acetate (20 mL)

Sources & evidence

ORD record
ord-eead7b2cec944866994062eeb52bd5c5
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

Loading…