Diisobutylaluminum hydride → (3R)-N-(benzyloxy)-6-cyclohexyl-3-(4-formyl-1,3-oxazol-2-yl)hexanamide

HRID 2084499노트

반응식

HRID 2084499 반응식
[CH2:1]([O:8][NH:9][C:10](=[O:32])[CH2:11][C@H:12]([C:22]1[O:23][CH:24]=[C:25]([C:27](OCC)=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.C([O-])(O)=O.[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1.CCOC(C)=O.CO>[CH2:1]([O:8][NH:9][C:10](=[O:32])[CH2:11][C@H:12]([C:22]1[O:23][CH:24]=[C:25]([CH:27]=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 14487Diisobutylaluminum hydrideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 60077661ethyl 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-1,3-oxazole-4-carboxylate

생성물 1

HCID 60077589(3R)-N-(benzyloxy)-6-cyclohexyl-3-(4-formyl-1,3-oxazol-2-yl)hexanamide수율 45%

시약·촉매·용매 3

HCID 887Methanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of ethyl 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-1,3-oxazole-4-carboxylate (preparation 155) (1.50 g, 3.39 mmol) in toluene (50 ml) at −78° C. was treated dropwise with DIBAL (1M in hexanes) (11.86 ml, 11.86 mmol) and stirred at this temperature for 30 minutes. MeOH (12 ml) was added to quench the reaction and the reaction mixture allowed to warm to room temperature. Alternate portions of NaHCO3 and MgSO4 were added to the reaction mixture to form a white paste. EtOAc was added and the solid filtered off. The solvent was removed under reduced pressure. The crude material was purified on a silica column eluting with a solvent gradient of EtOAc:pentane (1:1) gradually changing to (1:0) to afford the title compound as a colourless oil (605 mg, 45%).

후처리

  1. customto quench
  2. customthe reaction
  3. additionwere added to the reaction mixture
  4. customto form a white paste
  5. filtrationthe solid filtered off
  6. customThe solvent was removed under reduced pressure
  7. customThe crude material was purified on a silica column
  8. washeluting with a solvent gradient of EtOAc:pentane (1:1)

출처 및 근거

ORD 기록
ord-5accded2cd994e76a5ab098921a60370
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716861B2

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