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

HRID 1350259ノート

反応式

HRID 1350259 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-9f8f4f6db00b4774ae61bee3aadf557f
出典データセット
uspto-grants-2007_05
特許番号
US07214694B2

反応ノート

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