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Methanol → 2-(S)-{[7-(4-Fluoro-phenoxy)-4-hydroxy-1-methyl-isoquinoline-3-carbonyl]-amino}-propionic acid

HRID 1618178
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1618178
C(O[C:6]([C:8]1[N:9]=[C:10]([CH3:27])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.[NH2:28][C@H:29]([C:31]([OH:33])=[O:32])[CH3:30].CO[Na].CO>>[F:26][C:23]1[CH:22]=[CH:21][C:20]([O:19][C:13]2[CH:12]=[C:11]3[C:16]([C:17]([OH:18])=[C:8]([C:6]([NH:28][C@@H:29]([CH3:30])[C:31]([OH:33])=[O:32])=[O:7])[N:9]=[C:10]3[CH3:27])=[CH:15][CH:14]=2)=[CH:25][CH:24]=1
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Komponenten

5

Edukt 4

HCID 887MethanolHCID 5950L-AlanineHCID 667130617-(4-Fluoro-phenoxy)-4-hydroxy-1-methyl-isoquinoline-3-carboxylic acid butyl esterHCID 178418582HCID 178418582, Verbindung

Produkt 1

HCID 667132922-(S)-{[7-(4-Fluoro-phenoxy)-4-hydroxy-1-methyl-isoquinoline-3-carbonyl]-amino}-propionic acidAusbeute 71,8 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 7-(4-Fluoro-phenoxy)-4-hydroxy-1-methyl-isoquinoline-3-carboxylic acid butyl ester (92 mg, 0.25 mmol), (S)-alanine (225 mg, 2.5 mmol) and a 0.5 N solution of MeONa in MeOH (5 ml, 2.5 mmol) was heated in a microwave oven with stirring for 20 min at 140° C. before the mixture was concentrated in vacuo. To the residue was added water (10 ml) and the mixture was washed with EtOAc (2×25 ml). The so purified aq. solution was acidified by the addition of 6 N HCl and extracted with EtOAc (1×25 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a tan solid (69 mg); MS-(+)-ion M+1=385.1.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. additionTo the residue was added water (10 ml)
  3. washthe mixture was washed with EtOAc (2×25 ml)
  4. customThe so purified aq. solution
  5. additionwas acidified by the addition of 6 N HCl
  6. extractionextracted with EtOAc (1×25 ml)
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3604cf5bfa1e498c9dcaf302dbd0a3a3
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765956B2

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