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Sodium triacetoxyborohydride → HCID 178516677, Verbindung

HRID 1013851
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1013851
C([C@@H:8]1[CH2:12]OC(=O)[N:9]1[C:14](=[O:35])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][C:21]=1[Cl:34])CC=O)C1C=CC=CC=1.[NH:36]1[C:44]2[CH2:43][CH2:42][C@H:41](N)[CH2:40][C:39]=2[CH:38]=[N:37]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[Cl:34][C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH:24]=[C:25]([Cl:26])[C:20]=1[CH2:19][C@@H:15]1[CH2:12][CH2:8][N:9]([C@H:41]2[CH2:42][CH2:43][C:44]3[C:39](=[CH:38][NH:37][N:36]=3)[CH2:40]2)[C:14]1=[O:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 27973891(S)-4,5,6,7-Tetrahydro-1H-indazol-5-amineHCID 57671350(R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(3,5-dichloro-4'-fluoro-biphenyl-4-ylmethyl)-4-oxo-butyraldehyde

Produkt 1

HCID 178516677HCID 178516677, VerbindungAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

Add (R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(3,5-dichloro-4′-fluoro-biphenyl-4-ylmethyl)-4-oxo-butyraldehyde (Preparation 94) (1.13 mmoles; 580.00 mg) (dissolved in 5 ml dichloromethane) to (S)-(4,5,6,7-tetrahydro-1H-indazol-5-yl)amine 1.13 mmoles; 154.69 mg) dissolved in 5 ml Acetonitrile (5 mL). Cool the mixture in an ice water bath and add sodium triacetoxyborohydride (3.38 mmoles; 716.94 mg) portion wise. Remove the cooling bath and warm the mixture to ambient. Cool the mixture in an ice water bath and quench with 10 ml saturated sodium bicarbonate. Add 15 ml of ethyl acetate followed by 10 ml of brine. Charge the solution to a separatory funnel and separate the organic layer, dry over magnesium sulfate, filter, and concentrate to ⅓ volume. Add a seed crystal of (R)-3-(3,5-Dichloro-4′-fluoro-biphenyl-4-ylmethyl)-1-(S)-4,5,6,7-tetrahydro-2H-indazol-5-yl-pyrrolidin-2-one. Stir the solution at ambient temperature for 16 hours. Crystallization occurs and cool the mixture in an ice-water bath. Filter the cold mixture, collect the solid, and dry to give 284 mg of a white solid-crop A. LCMS=100% (M+1) at 458 amu. To the filtrate (now dry after evaporation), add 10 ml of MTBE to crystallize the rest of the product to obtain 89 mg white solid-crop B. LCMS=100% (M+1) at 458 amu 0.373/0.52=71.7%.

Aufarbeitung

  1. temperatureCool the mixture in an ice water bath
  2. customRemove the cooling bath
  3. temperaturewarm the mixture to ambient
  4. temperatureCool the mixture in an ice water bath
  5. customquench with 10 ml saturated sodium bicarbonate
  6. additionAdd 15 ml of ethyl acetate
  7. additionCharge the solution to a separatory funnel
  8. customseparate the organic layer
  9. dry with materialdry over magnesium sulfate
  10. filtrationfilter
  11. concentrationconcentrate
  12. additionAdd a seed crystal of (R)-3-(3,5-Dichloro-4′-fluoro-biphenyl-4-ylmethyl)-1-(S)-4,5,6,7-tetrahydro-2H-indazol-5-yl-pyrrolidin-2-one
  13. customCrystallization
  14. temperaturecool the mixture in an ice-water bath
  15. filtrationFilter the cold mixture
  16. customcollect the solid
  17. customdry

Quellen und Nachweise

ORD-Eintrag
ord-2ba42319e57749c99ebbfc4676ecb86e
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07981918B2

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