3-吲哚丁酸 → N-Methyl-N-Methoxy-4-(3-indolyl)butyramide

HRID 53563

反应方程式

HRID 53563 反应方程式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:2]1.[CH:16](N(CC)C(C)C)(C)C.Cl.[CH3:26][N:27](C)[OH:28].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(#N)C>[CH3:26][N:27]([O:28][CH3:16])[C:13](=[O:15])[CH2:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

参与物

6

反应物 4

HCID 86173-吲哚丁酸HCID 27969N,N-二甲基羟胺 盐酸盐HCID 81531N,N-二异丙基乙胺HCID 151348卡特缩合剂

产物 1

HCID 11107631N-Methyl-N-Methoxy-4-(3-indolyl)butyramide收率 94.3%

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂

实验过程

To a slurry of 1.75 g (8.61 mmol) of 3-indolebutyric acid (Aldrich Chemical Co.) in acetonitrile at room temperature was added 7.0 mL (40.2 mmol) of N,N-diisopropylethylamine, 1.0 g (10.3 mmol) of N,N-dimethylhydroxylamine hydrochloride and 4.19 g (9.5 mmol) of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) and the resulting mixture was allowed to stir at room temperature overnight and was then concentrated to dryness. The residue was dissolved into ethyl acetate and washed with water, 0.5N HCl, saturated NaHCO3 and brine and then dried over MgSO4 and concentrated. Flash chromatography (elution with a gradient of 2-10% ether in methylene chloride) provided 2.0 g of the amide 139. 1H NMR consistent with structure.

后处理

  1. concentrationwas then concentrated to dryness
  2. dissolutionThe residue was dissolved into ethyl acetate
  3. washwashed with water, 0.5N HCl, saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. washFlash chromatography (elution with a gradient of 2-10% ether in methylene chloride)

来源与证据

ORD记录
ord-335b9dd89de54030898409aded9b82d1
来源数据集
uspto-grants-1997_04
专利号
US05620971

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