L-Isoserine → 2-(S)-Hydroxy-3-{[4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carbonyl]-amino}-propionic acid

HRID 1481113Notes

Reaction equation

HRID 1481113 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][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:25][CH2:26][C@H:27]([OH:31])[C:28]([OH:30])=[O:29].C[O-].[Na+].CO>>[OH:31][C@@H:27]([CH2:26][NH:25][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][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH:9]=2)=[O:4])[C:28]([OH:30])=[O:29]

Participants

4

Reactant 3

HCID 6999797L-IsoserineHCID 23694274Sodium methanolate methanolHCID 898128354-Hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 898131782-(S)-Hydroxy-3-{[4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carbonyl]-amino}-propionic acidYield 45.2%

Procedure

A mixture of 4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.31 mmol) and 3-amino-2-(S)-hydroxy-propionic acid (97 mg, 0.92 mmol) in 0.5 M NaOMe/MeOH solution (1.23 mL, 0.62 mmol) was microwaved at 120° C. for 2 h. After cooled, solid precipitate was collected and rinsed with cold MeOH (1 mL). Solid was dissolved in water (40 mL), acidified by 1 N HCl to pH=3-4 and extracted with EtOAc. Organic layer was dried over MgSO4, filtered and concentrated to provide the title compound 54 mg (0.14 mmol) in 15% yield. LC-MS ESI−: 397.02 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 2 h
  2. temperatureAfter cooled
  3. customsolid precipitate was collected
  4. washrinsed with cold MeOH (1 mL)
  5. dissolutionSolid was dissolved in water (40 mL)
  6. extractionextracted with EtOAc
  7. dry with materialOrganic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ede54b814ca04f49b759bbb77d5c71e4
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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