4-Amino-2-hydroxybutyric acid, (S)-(-)- → HCID 89812850, compound

HRID 1481039Notes

Reaction equation

HRID 1481039 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](OC)=[O:22])[N:4]=1)#[N:2].[NH2:25][CH2:26][CH2:27][C@H:28]([OH:32])[C:29]([OH:31])=[O:30].C[O-].[Na+]>COCCO>[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:25][CH2:26][CH2:27][C@H:28]([OH:32])[C:29]([OH:31])=[O:30])=[O:22])[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 27339294-Amino-2-hydroxybutyric acid, (S)-(-)-HCID 10942334Sodium MethoxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89812850HCID 89812850, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate (200 mg, 0.63 mmol), (S)-4-amino-2-hydroxybutanoic acid (372 mg, 3.13 mmol, Sigma-Aldrich) and sodium methoxide (155 mg, 2.87 mmol) were suspended in 2-methoxyethanol (7 mL). The resulting mixture was heated to reflux for 3 hours and then cooled to room temperature. The solvent was removed in vacuo and the residue was dissolved in H2O (20 mL) and EtOAc (20 mL). To the stirred mixture was added 1 N hydrochloric acid until pH was 1. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-20% MeOH/CH2Cl2 with 0.5% formic acid) to give the title compound in 180 mg. MS: (−) m/z 406.28 (M−1).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in H2O (20 mL)
  5. additionTo the stirred mixture was added 1 N hydrochloric acid until pH was 1
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted twice with EtOAc
  8. dry with materialThe combined organic layers were dried over MgSO4
  9. concentrationconcentrated
  10. custompurified by flash chromatography (0-20% MeOH/CH2Cl2 with 0.5% formic acid)

Sources & evidence

ORD record
ord-ccbb387a99cc44d2b5a372e92128c192
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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