Iodine → HCID 58237928, 화합물

HRID 1192922노트

반응식

HRID 1192922 반응식
[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

참가 물질

6

반응물 3

HCID 807IodineHCID 7748Ethyl bromoacetateHCID 58200034HCID 58200034, 화합물

생성물 1

HCID 58237928HCID 58237928, 화합물수율 31%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8e559fe8e7674cde981eae2b157d4872
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680281B2

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