Sulfuric acid tetrahydrofuran → HCID 178487612, compound

HRID 2202327Notes

Reaction equation

HRID 2202327 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]([C:42]([OH:44])=[O:43])[CH2:39]3)=[O:37])[CH2:34][CH2:33][C:32]3[N:31]=[C:30]([O:45][CH3:46])[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]([C:42]([OH:44])=[O:43])[CH2:39]3)=[O:37])[CH2:34][CH2:33][C:32]3[N:31]=[C:30]([O:45][CH3:46])[CH:29]=[CH:28][C:27]2=3)=[O:25])[CH:15]=[C:16]2[C:20]=1[C:19]([CH3:21])([CH3:22])[CH2:18][CH2:17]2

Participants

4

Reactant 2

HCID 68124251Sulfuric acid tetrahydrofuranHCID 178487610HCID 178487610, compound

Product 1

HCID 178487612HCID 178487612, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.126M Sulfuric acid/THF (8.01 mL, 1.01 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)cyclobutanecarboxylic acid (500 mg, 1.01 mmol) in THF (10 mL) at room temperature. The mixture was concentrated under reduced pressure to dryness, and the solid was collected by filtration with ethyl acetate (10 mL) to give the title compound (548.3 mg, 0.924 mmol, 92%) 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 (10 mL)

Sources & evidence

ORD record
ord-61955618f7a2421bbcb922a1cfb807fe
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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