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

HRID 529696ノート

反応式

HRID 529696 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-4219424d90d0400194b0fc7d65e01753
出典データセット
uspto-grants-2016_05
特許番号
US09346825B2

反応ノート

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