Methanol → 2-(S)-Hydroxy-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid

HRID 1480933Notes

Reaction equation

HRID 1480933 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].[OH:23][C@@H:24]([CH2:28][NH2:29])[C:25]([OH:27])=[O:26].CO>C[O-].[Na+]>[OH:23][C@@H:24]([CH2:28][NH:29][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:25]([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 887MethanolHCID 6999797L-IsoserineHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 717351402-(S)-Hydroxy-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (90 mg, 0.31 mmol) and 2-(S)-hydroxy-3-amino-propionic acid (Sigma-Aldrich) (96 mg, 0.92 mmol) in 0.5 N NaOMe in MeOH solution (1.22 mL, 0.61 mmol) was microwaved at 120° C. for 1 h and concentrated. Residue was dissolved in water (70 mL) and acidified by 1 N HCl solution to pH=3-4. It was extracted with EtOAc, Organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give the title compound (105 mg, 0.29 mmol) in 92% yield. LC-MS ESI−: 366.99 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 1 h
  2. concentrationconcentrated
  3. dissolutionResidue was dissolved in water (70 mL)
  4. extractionIt was extracted with EtOAc, Organic layer
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-316329ae4d7643ca975d302c89961bdf
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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