Iodine → HCID 58237928、化合物

HRID 1192922ノート

反応式

HRID 1192922 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:21])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.II.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>C1COCC1.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]([C:11]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:17])[CH2:18][CH2:19][C:20]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)([OH:21])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH3:9])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 807IodineHCID 7748Ethyl bromoacetateHCID 58200034HCID 58200034、化合物

生成物 1

HCID 58237928HCID 58237928、化合物収率 31%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred suspension of (S)-tert-butyl 1-(4-bromophenyl)ethyl(3-(4-fluorophenyl)-3-oxopropyl)carbamate (13 g, 28.9 mmol) and zinc powder (9.4 g, 0.144 mol) in THF (200 mL) at rt was added iodine (4.40 g, 0.173 mol) and ethyl bromoacetate (9.7 g, 57.7 mmol). The mixture was heated at reflux for 2 h, and quenched by addition of water. The mixture was filtered through a celite pad, the filtrate was extracted with EtOAc. The organic phase was concentrated to give the crude product, which was purified by column chromatography to afford ethyl 5-(((S)-1-(4-bromophenyl)ethyl)(tert-butoxycarbonyl)amino)-3-(4-fluorophenyl)-3-hydroxypentanoate (4.8 g, 31%). 1H NMR (CDCl3): δ 1.02 (t, 3H), 1.29-1.41 (m, 12H), 1.88 (m, 1H), 2.51-2.73 (m, 3H), 2.99 (m, 1H), 3.96 (q, 2H), 4.03 (m, 1H), 4.36 (m, 1H), 4.77 (m, 1H), 5.33 (m, 1H), 6.88-6.96 (m, 4H), 7.11 (m, 2H), 7.24 (m, 1H), 7.36 (m, 3H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customquenched by addition of water
  4. filtrationThe mixture was filtered through a celite pad
  5. extractionthe filtrate was extracted with EtOAc
  6. concentrationThe organic phase was concentrated
  7. customto give the crude product, which
  8. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-8e559fe8e7674cde981eae2b157d4872
出典データセット
uspto-grants-2014_03
特許番号
US08680281B2

反応ノート

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