Methanamine, N-methoxy-, hydrochloride (1:1) → (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamate

HRID 1098866

반응식

HRID 1098866 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:17][NH:18][O:19][CH3:20].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C.O>[CH3:20][O:19][N:18]([CH3:17])[C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH2:14][CH3:15]

참가 물질

8

반응물 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2733748(2S)-2-(((tert-butoxy)carbonyl)amino)pentanoic acid

생성물 1

HCID 9992774(S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Commercially available (2S)-2-[(tert-butoxycarbonyl)amino]pentanoic acid (1.0 g, 4.6 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.47 g, 4.8 mmol) were dissolved in DMF (18 ml). O-benzotriazole-1-yl-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate (1.92 g, 5.06 mmol) and N,N-diisopropylethylamine (2.47 ml, 14.5 mmol) were added. The reaction was stirred at r.t. over night. The reaction was poured into a mixture of water and ethyl acetate. The mixture was shaken, the layers separated and the water layer washed twice with ethyl acetate. The collected organic phase was washed with a small portion of water and dried over sodium sulphate. The solvent was removed under educed pressure and the crude product was purified by flash chromatography.

후처리

  1. stirringThe mixture was shaken
  2. customthe layers separated
  3. washthe water layer washed twice with ethyl acetate
  4. washThe collected organic phase was washed with a small portion of water
  5. dry with materialdried over sodium sulphate
  6. customThe solvent was removed
  7. customthe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-0db9bf0e087d48f891cbf993d7a9dc0c
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143290B2

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