Methanol → HCID 131736614, compound

HRID 1481040Notes

Reaction equation

HRID 1481040 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21]([NH:23][CH2:24][CH2:25][C@H:26]([OH:30])[C:27]([OH:29])=[O:28])=[O:22])[N:4]=1)#[N:2].[CH3:31]O>OS(O)(=O)=O>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21]([NH:23][CH2:24][CH2:25][C@H:26]([OH:30])[C:27]([O:29][CH3:31])=[O:28])=[O:22])[N:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 89812850HCID 89812850, compound

Product 1

HCID 131736614HCID 131736614, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of (S)-4-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-2-hydroxybutanoic acid (73 mg, 0.18 mmol) in anhydrous MeOH (25 mL) was added concentrated H2SO4 (3 drops). The resulting mixture was heated to reflux for 20 hours. The volatiles were removed in vacuo and the residue was purified by flash chromatography (0-30% EtOAc/CH2Cl2) to give the title compound in 54 mg. MS: (−) m/z 420.26 (M−1).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 20 hours
  3. customThe volatiles were removed in vacuo
  4. customthe residue was purified by flash chromatography (0-30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-ff4301df9ddb452eb0e6dc000d368758
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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