Triethylamine → Tert-butyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamate

HRID 1725193Notes

Reaction equation

HRID 1725193 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].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:12](=[O:14])[N:17]([O:18][CH3:19])[CH3:16])[CH2:10][CH2:11]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 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-butoxycarbonylaminocyclopropanecarboxylic acid (2.32 g, 11.5 mmol) in CH2Cl2 (25 mL) at 0° C. was added N,O-dimethylhydroxylamine hydrochloride (1.24 g, 12.7 mmol), triethylamine (2.57 g, 3.54 mL, 25.4 mmol), and HATU (4.82 g, 12.7 mmol). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated under reduced pressure and then partitioned between Et2O and water. The water layer was extracted with Et2O. The combined organic layer was washed with brine, dried (Na2SO4), and concentrated under reduced pressure to yield [1-(methoxy-methyl-carbamoyl)-cyclopropyl]carbamic acid tert-butyl ester which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompartitioned between Et2O and water
  3. extractionThe water layer was extracted with Et2O
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-801d173a0d1e40b39ec67e7755642f47
Source dataset
uspto-grants-2009_02
Patent number
US07488848B2

Reaction notes

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