Sodium Hydroxide → 9-Bromo-10-fluoro-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532887
[Br:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:17](=[O:27])[CH2:18][NH:19][C:20](OC(C)(C)C)=[O:21])[CH:7]2[CH2:13]C(O)=O.BrC1C(F)=CC=C2C=1CCN(C(=O)CNC(OC(C)(C)C)=O)C2CC(OC)=O.[OH-].[Na+]>CCO>[Br:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:17](=[O:27])[CH2:18][NH:19][C:20](=[O:21])[CH:13]=[C:7]12

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 86711337Methyl 2-(5-bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetateHCID 867113382-(5-Bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid

Produkt 1

HCID 867113419-Bromo-10-fluoro-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-(5-bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid. To a stirred solution of methyl 2-(5-bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate (62.6 g, 136 mmol) in EtOH (500 mL), 4N aqueous NaOH (39.5 mL, 158 mmol) was added and the solution was stirred at RT for 2 h. The white precipitate was filtered off and the white solid was washed with a small amount of EtOH (1×) and diethyl ether (2×). The sodium salt was partitioned between 0.5N aqueous HCl and DCM, the organic layer was separated and washed with 0.5N aqueous HCl (1×) and brine (1×). The combined organic layers were dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was dried under high vacuo overnight to yield the title compound as white foam (58.45 g). UPLC-MS: MS 445.2/447.2 (M+H+); UPLC rt 0.99 min.

Aufarbeitung

  1. filtrationThe white precipitate was filtered off
  2. washthe white solid was washed with a small amount of EtOH (1×) and diethyl ether (2×)
  3. customThe sodium salt was partitioned between 0.5N aqueous HCl and DCM
  4. customthe organic layer was separated
  5. washwashed with 0.5N aqueous HCl (1×) and brine (1×)
  6. dry with materialThe combined organic layers were dried with sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was dried under high vacuo overnight

Quellen und Nachweise

ORD-Eintrag
ord-8ae8e326ef2b4ce187d495534417910b
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853203B2

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