Allyl bromide → HCID 58109363、化合物

HRID 2037535ノート

反応式

HRID 2037535 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][OH:25])[O:19][C:18]2=[O:33])[CH3:16])=[CH:11][CH:10]=1.[H-].[Na+].[CH2:36](Br)[CH:37]=[CH2:38]>C1COCC1>[CH2:38]([O:25][CH2:24][CH2:23][C@@:20]1([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=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)[CH:37]=[CH2:36]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 53361128HCID 53361128、化合物

生成物 1

HCID 58109363HCID 58109363、化合物収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran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-hydro-xyethyl)-1,3-oxazinan-2-one (100 mg, 0.22 mmol) in THF (5 mL) was added NaH (30 mg, 1.10 mmol) at 0° C. After stirring for 1 h, allyl bromide (79 mg, 0.66 mmol) was added, and the mixture was stirred at rt overnight. The reaction was quenched with water, and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC to give (S)-6-(2-(allyloxy)ethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (100 mg, 92%) 1H NMR (CDCl3): 1.47-1.59 (d, 3H), 2.05-2.15 (m, 2H), 2.21-2.38 (m, 3H), 2.88-2.93 (m, 1H), 3.12-3.19 (m, 1H), 3.52-3.59 (m, 1H). 3.62-3.85 (m, 2H), 5.03-5.18 (m, 2H), 5.61-5.69 (m, 1H), 5.71-5.81 (m, 1H), 6.81-6.92 (m, 3H), 6.92-7.01 (m, 2H), 7.13-7.20 (m, 4H), 7.21-7.26 (m, 3H).

後処理

  1. stirringthe mixture was stirred at rt overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative TLC

出典と根拠

ORDレコード
ord-c7548eb643fb4f2198d149cd6020f58c
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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