Indole-3-Butyric Acid → N-Methyl-N-Methoxy-4-(3-indolyl)butyramide

HRID 53563

반응식

HRID 53563 반응식
[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

참가 물질

6

반응물 4

HCID 8617Indole-3-Butyric AcidHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-335b9dd89de54030898409aded9b82d1
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620971

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