Diisopropylethylamine → HCID 178456099、化合物

HRID 331481ノート

反応式

HRID 331481 の反応式
[OH:1][C@H:2]([CH2:8][CH3:9])[CH2:3][C:4](OC)=[O:5].C[Si](C)(C)[O-].[K+].C(N(CC)C(C)C)(C)C.Cl.Cl.[O:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[C:35]([CH:36]3[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][C@H:44]4[CH2:49][CH2:48][C@H:47]([NH2:50])[CH2:46][CH2:45]4)[CH2:38][CH2:37]3)[C:30]=2[CH2:29][CH2:28]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([O-])(O)=O.[Na+]>O1CCOCC1>[O:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[C:35]([CH:36]3[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][C@H:44]4[CH2:45][CH2:46][C@H:47]([NH:50][C:4](=[O:5])[CH2:3][C@H:2]([OH:1])[CH2:8][CH3:9])[CH2:48][CH2:49]4)[CH2:38][CH2:37]3)[C:30]=2[CH2:29][CH2:28]1

参加物

8

反応物 6

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11804797(-)-Methyl (R)-3-hydroxyvalerateHCID 23668039Potassium trimethylsilanolateHCID 178478710HCID 178478710、化合物2 回

生成物 1

HCID 178456099HCID 178456099、化合物収率 54.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of (R)-methyl 3-hydroxypentanoate (49.4 mg, 48 μl, 0.374 mmol) in dioxane (3 ml) was added at room temperature potassium trimethylsilanolate (63.9 mg, 0.5 mmol) and the mixture was allowed to stir for additional 23 h. Afterwards N,N-diisopropylethyl-amine (177 mg, 1.37 mmol), trans-4-{2-[4-(2,3-dihydro-benzofuran-4-yl)-piperidin-1-yl]-ethyl}-cyclohexylamine dihydrochloride (intermediate B) (100 mg, 0.25 mmol) and TBTU (120 mg, 0.374 mmol) were added, and the mixture was allowed to stir for 3 h at room temperature. The reaction mixture was poured into saturated NaHCO3 solution (20 ml) and extracted with dichloromethane (2×40 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. The crude material (140 mg) was further purified by flash chromatography on silica gel (dichloromethane/MeOH 9:1) to yield the title compound as white solid (58 mg, 54%), MS (ISP) m/z=429.4 [(M+H)+], mp 201° C.

後処理

  1. stirringto stir for 3 h at room temperature
  2. extractionextracted with dichloromethane (2×40 ml)
  3. washThe combined organic layers were washed with brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude material (140 mg) was further purified by flash chromatography on silica gel (dichloromethane/MeOH 9:1)

出典と根拠

ORDレコード
ord-b64dd76386c24690b8705a21a1b6e18c
出典データセット
uspto-grants-2014_11
特許番号
US08877778B2

反応ノート

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