Hydrochloric Acid → (4S)-2,8-Dimethyl-4-[(toluenesulfonyl)amino]-5-nonanone

HRID 1904207

반응식

HRID 1904207 반응식
[NH:1]([S:10]([C:13]1[CH:19]=[CH:18][C:16](C)=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[CH2:20]([Li])CCC.[CH2:25]([Mg]Br)[CH2:26][CH:27]([CH3:29])[CH3:28].Cl>C1COCC1.CCCCCC>[CH3:6][CH:4]([CH2:3][C@H:2]([NH:1][S:10]([C:13]1[C:14]([CH3:20])=[CH:15][CH:16]=[CH:18][CH:19]=1)(=[O:11])=[O:12])[C:7](=[O:9])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 768170(2S)-4-methyl-2-(4-methylbenzenesulfonamido)pentanoic acidHCID 178418339ButyllithiumHCID 178418529HCID 178418529, 화합물

생성물 1

HCID 70040285(4S)-2,8-Dimethyl-4-[(toluenesulfonyl)amino]-5-nonanone수율 41%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To a stirred -78° C. solution of Ts-Leu (15 g, 53 mmol) in dry THF (240 ml) was added n-butyl lithium (57.8 ml of a 0.91M solution in hexane) followed 15 minutes later by isopentyl magnesium bromide (185 ml of a 0.8M solution in THF). The mixture was heated at reflux for 3 days, then cooled and poured into 0° C. 1M HCl (500 ml). The layers were separated and the aqueous phase was extracted with ether (3×150 ml). The combined organic layers were washed with saturated NaHCO3 (2×150 ml) and brine 150 ml). Drying and evaporating provided a residue which was chromatographed on silica gel to give 7.43 g (41%) of the desired product. Mass spectrum: (M+H)+ =340.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 days
  3. temperaturecooled
  4. additionpoured into 0° C
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with ether (3×150 ml)
  7. washThe combined organic layers were washed with saturated NaHCO3 (2×150 ml) and brine 150 ml)
  8. customDrying
  9. customevaporating
  10. customprovided a residue which
  11. customwas chromatographed on silica gel

출처 및 근거

ORD 기록
ord-be710d8e99bc4166a37484d9bfe64e41
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04837204

연결된 노트

불러오는 중…