1-Hydroxybenzotriazole → tert-Butyl 2-(methoxy(methyl)amino)-1-methyl-2-oxoethylcarbamate

HRID 1726375Notes

Reaction equation

HRID 1726375 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:15][NH:16][O:17][CH3:18].Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:10](=[O:12])[N:16]([O:17][CH3:18])[CH3:15])[CH3:13])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2684712-N-Boc-aminopropionic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 375613tert-Butyl 2-(methoxy(methyl)amino)-1-methyl-2-oxoethylcarbamateYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-t-butoxycarbonylamino-propionic acid (25 g, 132 mmole) was dissolved in dimethylformamide (DMF, 300 ml). N,O-dimethylhydroxylamine HCl (12.9 g, 132 mmol) was added, followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl (26.6 g, 139.0 mmol), HOBT (17.8 g, 132 mmol), and NaHCO3 (44.4 g, 528 mmol). The reaction mixture was stirred under nitrogen for 48 h. The solution was then filtered, and the solvent evaporated under reduced pressure. The residue was dissolved in CH2Cl2 and washed with 2% aqueous HCl, saturated aqueous NaHCO3, and water. The organic layers were dried over sodium sulfate and evaporated under reduced pressure to provide [1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (intermediate XIIIa, 12.84 g, 42%). M+=233.

Workup

  1. filtrationThe solution was then filtered
  2. customthe solvent evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with 2% aqueous HCl, saturated aqueous NaHCO3, and water
  5. dry with materialThe organic layers were dried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-57797039abaa4f9ab92a6127f7ed6ec9
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

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