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

HRID 13105

Reaction equation

HRID 13105 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c2f7670bf3e743c695ef9de335ddfdac
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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