tert-Butylsulfinamide, (R)-(+)- → tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]-N-[(4E)-4-[(R)-tert-butylsulfinyl]imino-4-phenylbutyl]carbamate

HRID 219611노트

반응식

HRID 219611 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[C:29]([S@:33]([NH2:35])=[O:34])([CH3:32])([CH3:31])[CH3:30]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20]/[C:21](=[N:35]\[S@@:33]([C:29]([CH3:32])([CH3:31])[CH3:30])=[O:34])/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 59190380(S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate

생성물 1

HCID 88542676tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]-N-[(4E)-4-[(R)-tert-butylsulfinyl]imino-4-phenylbutyl]carbamate수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate (3.14 g, 7.04 mmol), (R)-t-Butylsulfinamide, Ti(OEt)4 (125 μL, 1.5 equiv) were mixed with dry THF (80 mL) and heated at reflux for overnight. LC-MS found most of starting material was consumed. The mixture was diluted with ether (200 mL), washed with water (50 mL), brine (30 mL), dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 120-g silica gel cartridge, eluted with a 10˜35% EtOAc in hexanes gradient, to afford tert-butyl (S)-1-(4-bromophenyl)ethyl((E)-4-((R)-tert-butylsulfinylimino)-4-phenylbutyl)carbamate (1.97 g, 51%) product and recovered starting material (0.72 g). LC-MS Method 1 tR=2.43 min, m/z 549, 551 (M+1)

후처리

  1. temperatureheated
  2. temperatureat reflux for overnight
  3. customwas consumed
  4. additionThe mixture was diluted with ether (200 mL)
  5. washwashed with water (50 mL), brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified by chromatography on a 120-g silica gel cartridge
  9. washeluted with a 10˜35% EtOAc in hexanes gradient

출처 및 근거

ORD 기록
ord-a06e3981d2844da3a2bf0330af91f491
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202857B2

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