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

HRID 219611ノート

反応式

HRID 219611 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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)

後処理

  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

出典と根拠

ORDレコード
ord-a06e3981d2844da3a2bf0330af91f491
出典データセット
uspto-grants-2012_06
特許番号
US08202857B2

反応ノート

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