Pyridine → HCID 58109643、化合物

HRID 2037531ノート

反応式

HRID 2037531 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@@:20]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)([CH2:23][CH2:24]O)[O:19][C:18]2=[O:33])[CH3:16])=[CH:11][CH:10]=1.N1C=CC=CC=1.P(Br)(Br)[Br:41]>C(Cl)Cl>[Br:41][CH2:24][CH2:23][C@@:20]1([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[O:19][C:18](=[O:33])[N:17]([C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[CH:10][CH:11]=2)[CH3:16])[CH2:22][CH2:21]1

参加物

5

反応物 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 53361128HCID 53361128、化合物

生成物 1

HCID 58109643HCID 58109643、化合物収率 41.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (250 mg, 0.55 mmol) in methylene chloride (10 mL) was added pyridine (0.5 mL) and PBr3 (75 mg). The formed mixture was stirred for 2 h. The mixture was washed with water. The organic phase was separated, and concentrated to give the crude product, which was purified by preparative TLC to afford (S)-6-(2-bromoethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (60 mg, 23%). 1H NMR: (400 MHz, CDCl3): δ=1.45 (d, 3H), 2.12-2.38 (d, 4H), 2.43 (m, 1H), 2.94 (m, 2H), 3.49 (m, 1H), 5.22 (m, 1H), 6.83 (m, 2H), 6.95 (m, 4H), 7.19 (m, 1H), 7.22 (m, 2H).

後処理

  1. washThe mixture was washed with water
  2. customThe organic phase was separated
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by preparative TLC

出典と根拠

ORDレコード
ord-268ce89de01f43d8966d1873a984a42f
出典データセット
uspto-grants-2013_11
特許番号
US08575156B2

反応ノート

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