Methanamine, N-methoxy-, hydrochloride (1:1) → Tert-butyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamate

HRID 1877698Notes

Reaction equation

HRID 1877698 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]([OH:14])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16][NH:17][O:18][CH3:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:19][O:18][N:17]([CH3:16])[C:12]([C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11]1)=[O:14]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 15234151Tert-butyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonylamino)cyclopropanecarboxylic acid (11.00 g, 54.7 mmol, 1.0 eq) in methylene chloride at 0° C. was added N,O-dimethyl hydroxylamine HCl (5.9 g, 60.4 mmol, 1.1 eq), TEA (13.82 g, 13.6 mmol, 2.5 eq) and HATU (22.90 g, 60.2 mmol, 1.1 eq). The resulting reaction mixture was stirred at room temperature under an N2 atmosphere overnight. After TLC showed reaction was completed, the reaction mixture was concentrated, diluted with water and extracted with diethyl ether. The organic layer was washed with brine, dried over Na2SO4 and concentrated to get the desired product as a white solid. Yield: 13.00 g (97.52%).

Workup

  1. customThe resulting reaction mixture
  2. customreaction
  3. concentrationthe reaction mixture was concentrated
  4. additiondiluted with water
  5. extractionextracted with diethyl ether
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f02f3b3743e9438689d2b974566c119b
Source dataset
uspto-grants-2012_11
Patent number
US08309558B2

Reaction notes

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