Hydrazine → (2S)-2-[(S)-[3,5-Bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enehydrazide

HRID 529696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529696
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C@@H:13]([OH:31])[C@H:14]([CH:29]=[CH2:30])[C:15]([N:17]2[C@@H](C3C=CC=CC=3)COC2=O)=[O:16])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH2:34]N>C1COCC1>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C@@H:13]([OH:31])[C@H:14]([CH:29]=[CH2:30])[C:15]([NH:17][NH2:34])=[O:16])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 86682258(4S)-3-{(2S)-2-[(S)-[3,5-bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enoyl}-4-phenyl-1,3-oxazolidin-2-one

Produkt 1

HCID 86682260(2S)-2-[(S)-[3,5-Bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enehydrazideAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(4S)-3-{(2S)-2-[(S)-[3,5-Bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enoyl}-4-phenyl-1,3-oxazolidin-2-one (20 g, 42.5 mmol) and hydrazine (2.71 g, 85 mmol) in THF (100 mL) was stirred at room temperature for 1 hour. The reaction was diluted with ethyl acetate:hexanes (2:1, 200 mL) and was partitioned with water (100 mL). The organic was washed with brine (100 mL) and was dried over sodium sulfate, filtered, and concentrated. The crude product was triturated with IPA (30 mL) to remove the chiral auxiliary. The filtrate was concentrated to yield (2S)-2-[(S)-[3,5-bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enehydrazide (14.5 g, 42.4 mmol), which was used without further purification. 1H NMR (500 MHz, CDCl3) δ7.81 (s, 3H), 7.83 (s, 1H), 7.0 (br s, 1H), 5.9 (m, 1H), 5.42 (d, J=3.3 Hz, 1H), 5.29 (d, J=10.3 Hz, 1H), 5.03 (d, J=17.1 Hz, 1H), 3.1 (dd, J=9.4, 3.5 Hz, 1H).

Aufarbeitung

  1. customwas partitioned with water (100 mL)
  2. washThe organic was washed with brine (100 mL)
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was triturated with IPA (30 mL)
  7. customto remove the chiral auxiliary
  8. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4219424d90d0400194b0fc7d65e01753
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346825B2

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