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

HRID 529696노트

반응식

HRID 529696 반응식
[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

참가 물질

4

반응물 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

생성물 1

HCID 86682260(2S)-2-[(S)-[3,5-Bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enehydrazide수율 99.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-4219424d90d0400194b0fc7d65e01753
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346825B2

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