Hydrochloric Acid → (S)-2-[(6-Isopropoxy-1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid

HRID 250318

Reaktionsgleichung

Reaktionsgleichung von HRID 250318
[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([Cl:15])=[N:10][C:9]([C:16]([OH:18])=O)=[C:8]2[OH:19])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[O:45][C:46](=[O:50])[C@H:47]([CH3:49])[NH2:48].[OH-].[Na+].Cl>CO.O>[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([Cl:15])=[N:10][C:9]([C:16]([NH:48][C@@H:47]([CH3:49])[C:46]([OH:50])=[O:45])=[O:18])=[C:8]2[OH:19])([CH3:2])[CH3:3]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 82335L-Alanine methyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 542422501-Chloro-4-hydroxy-6-isopropoxy-isoquinoline-3-carboxylic acid

Produkt 1

HCID 86595458(S)-2-[(6-Isopropoxy-1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acidAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

0.030 g of 6-isopropoxy-1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid and 0.046 g of HATU were allowed to react with 0.017 g of L-Alanine methyl ester under analogous conditions to Example A-1 a). Treatment of the crude product ester with 0.014 g of NaOH in 0.1 ml of 1:1 methanol-water at room temperature for 2 days, followed by acidification to pH=2 with 1M hydrochloric acid, gave a solid product. The product was collected by filtration, washed with water, and dried to give 0.023 g of an off-white solid: MS-(−)-ion, M−1=353.0 amu.

Aufarbeitung

  1. customgave a solid product
  2. filtrationThe product was collected by filtration
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0ed315bc12c14421a015d790a1dea234
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863292B2

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