N,N-dimethylhydroxylamine hydrochloride → (S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester

HRID 990397Notes

Reaction equation

HRID 990397 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:17])[C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl.CN(C)O.CN([C:35]([O:39][N:40]1N=NC2C=CC=C[C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[N:8]([C@H:9]([C:14](=[O:16])[N:40]([O:39][CH3:35])[CH3:41])[CH2:10][CH:11]([CH3:12])[CH3:13])[CH3:17])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7010555(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acid

Product 1

HCID 53718737(S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-tert-butoxycarbonyl-N-methyl-L-leucine (5.0 g, 20.4 mmol) was dissolved in DMF (100 mL), treated with treated with N,N-diisopropylethylamine (28 mL, 163 mmol), N,N-dimethylhydroxylamine hydrochloride salt (2.0 g, 20.4 mmol), and HBTU (7.73 g, 20.4 mmol), then stirred overnight at room temperature. The reaction was diluted with EtOAc (500 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give the desired product as an oil; MS: 289.2 (M+1 for C14H28N2O4); TLC (SiO2) Rf 0.39 (8% MeOH/CH2Cl2), visualized with ninhydrin.

Workup

  1. additiontreated
  2. washwashed with saturated bicarbonate solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-35fb4a47a94e4e6e8e37ae931acaa064
Source dataset
uspto-grants-2002_10
Patent number
US06458781B1

Reaction notes

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