Hydrochloric Acid → HCID 89813101, compound

HRID 1480937Notes

Reaction equation

HRID 1480937 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:23][CH2:24][CH2:25][C@H:26]([OH:30])[C:27]([OH:29])=[O:28].CO.Cl>C[O-].[Na+].O>[OH:30][C@@H:26]([CH2:25][CH2:24][NH:23][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH:9]=2)=[O:4])[C:27]([OH:29])=[O:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 27339294-Amino-2-hydroxybutyric acid, (S)-(-)-HCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89813101HCID 89813101, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.34 mmol) and (S)-(−)-4-amino-2-hydroxybutyric acid (122 mg, 1.02 mmol) in 0.5 N NaOMe in MeOH solution (1.4 mL, 0.7 mmol) was microwaved at 120° C. for 1 h. Reaction mixture was diluted with water (100 mL), acidified by 1 N HCl aqueous solution to pH=3-4 and extracted with EtOAc. Organic layer was washed with brine, dried over Mg2SO4, filtered and concentrated to provide the title compound (120 mg, 0.31 mmol) in 92.4% yield. LC-MS ESI−: 381.05 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 1 h
  2. customReaction mixture
  3. extractionextracted with EtOAc
  4. washOrganic layer was washed with brine
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39e2580ab0cb452995d53875025a4fa0
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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