Tetrahydrofuran → Benzyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

HRID 263471노트

반응식

HRID 263471 반응식
[Cl:1][CH2:2]C(CCl)=O.[CH2:7]([O:14][C:15]([NH:17][C@H:18]([C:26]([OH:28])=O)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O1CCCC1.[BH4-].[Na+]>CO>[CH2:7]([O:14][C:15]([NH:17][C@@H:18]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C@H:26]([OH:28])[CH2:2][Cl:1])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 21117419N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone

생성물 1

HCID 10860587Benzyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate수율 43%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

To a solution of 75.0 g (0.226 mol) of N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone in a mixture of 807 mL of methanol and 807 mL, of tetrahydrofuran at -2° C., was added 13.17 g (0.348 mol, 1.54 equiv.) of solid sodium borohydride over one hundred minutes. The solvents were removed in vacuo at 40° C. and the residue dissolved in ethyl acetate (approx. 1L). The solution was washed sequentially with 1M potassium hydrogen sulfate, saturated sodium bicarbonate and then saturated sodium chloride solutions. After drying over anhydrous magnesium sulfate and filtering, the solution was removed in vacuo. To the resulting oil was added hexane (approx. 1L) and the mixture warmed to 60° C. with swirling. After cooling to room temperature, the solids were collected and washed with 2L of hexane. The resulting solid was recrystallized from hot ethyl acetate and hexane to afford 32.3 g (43% yield) of N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol, mp 150°-151° C. and M+Li+ =340. formula: ##STR49##

후처리

  1. customThe solvents were removed in vacuo at 40° C.
  2. dissolutionthe residue dissolved in ethyl acetate (approx. 1L)
  3. washThe solution was washed sequentially with 1M potassium hydrogen sulfate, saturated sodium bicarbonate
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. customthe solution was removed in vacuo
  7. additionTo the resulting oil was added hexane (approx. 1L)
  8. temperatureAfter cooling to room temperature
  9. customthe solids were collected
  10. washwashed with 2L of hexane
  11. customThe resulting solid was recrystallized from hot ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-564562754e98483a8ff06d8428068ecd
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643924

반응 노트

불러오는 중…