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Sodium Hydroxide → tert-butyl ((1S,4S)-4-(2-mercaptoethyl)-4-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)carbamate

HRID 1747132
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1747132
C(=O)([S:3][CH2:4][CH2:5][C@@:6]1([C:19]([N:21]2[CH2:30][CH2:29][C:28]3[N:27]=[CH:26][C:25]([C:31]([F:34])([F:33])[F:32])=[CH:24][C:23]=3[CH2:22]2)=[O:20])[CH2:10][C@H:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:8]=[CH:7]1)C.[OH-].[Na+]>CO>[SH:3][CH2:4][CH2:5][C@@:6]1([C:19]([N:21]2[CH2:30][CH2:29][C:28]3[N:27]=[CH:26][C:25]([C:31]([F:34])([F:33])[F:32])=[CH:24][C:23]=3[CH2:22]2)=[O:20])[CH2:10][C@H:9]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:8]=[CH:7]1
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Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 89856405S-(2-((1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)ethyl) ethanethioate

Produkt 1

HCID 86708139tert-butyl ((1S,4S)-4-(2-mercaptoethyl)-4-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

To a solution of the product of Step A (1.74 g, 3.39 mmol, 1 eq) in methanol (100 mL) at rt under Ar (degassed) was added 0.2 N NaOH (85 mL, 85 mmol, 5 eq) that was degassed by bubbling Ar through the solution prior to addition. After 2 hr, the methanol was concentrated, 6 N HCl was added until the solution was acidic, the aqueous was extracted with DCM, the organics combined, dried over MgSO4 and concentrated to afford the product of Step B which was used unpurified in the next step. Calculated for C22H28F3N3O3S: 494.2 (M+23). found: 494.1.

Aufarbeitung

  1. customwas degassed
  2. customby bubbling Ar through the solution
  3. additionto addition
  4. concentrationthe methanol was concentrated
  5. addition6 N HCl was added until the solution
  6. extractionthe aqueous was extracted with DCM
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-82bf0a1621394fc98eb290db127a6811
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150532B2

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