Triethylamine → HCID 13676801, compound

HRID 1040492Notes

Reaction equation

HRID 1040492 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]([OH:17])=O)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:19](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.C(=O)([O-])O.[NH4+]>CN(C=O)C.O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C:12]1([C:15](=[O:17])[NH2:19])[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14013Ammonium BicarbonateHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic 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 13676801HCID 13676801, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzyloxycarbonylamino-cyclopropanecarboxylic acid (7.0 g, 29.8 mmol) in DMF (30 mL) was added HATU (11.3 g, 29.8 mmol) and Et3N (4.3 mL, 29.8 mmol). The mixture was allowed to stir at room temperature for 20 min, then ammonium hydrogen carbonate (7.06 g, 89.3 mmol) was added in one portion. The reaction was heated at 60° C. for 12 h. The mixture was cooled to room temperature, diluted with water and extracted with EtOAc (2×100 mL). The combined extracts were washed with satd NaHCO3, water, brine and dried with MgSO4. The mixture was filtered and the solvent removed to give (1-carbamoyl-cyclopropyl)-carbamic acid benzyl ester (5.5 g, 24.5 mmol) as a white solid.

Workup

  1. temperatureThe reaction was heated at 60° C. for 12 h
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe combined extracts were washed with satd NaHCO3, water, brine
  5. dry with materialdried with MgSO4
  6. filtrationThe mixture was filtered
  7. customthe solvent removed

Sources & evidence

ORD record
ord-5a224b1755f7468285e3e3397fedb68c
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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