Ammonium Hydroxide → (1-Carbamoyl-cyclopropyl)-carbamic acid benzyl ester

HRID 1040440Notes

Reaction equation

HRID 1040440 reaction equation
[C:1](C1CC1(N)C(O)=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN(C(C)C)C(C)C.CN(C(ON1N=[N:42][C:37]2[CH:38]=[CH:39]C=[N:41][C:36]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[OH-:52]>CN(C=O)C>[CH2:4]([O:3][C:1](=[O:2])[NH:42][C:37]1([C:36](=[O:52])[NH2:41])[CH2:39][CH2:38]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67390283Cbz-1-aminocyclopropane-1-carboxylic acid

Product 1

HCID 13676801(1-Carbamoyl-cyclopropyl)-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a vial was added Cbz-1-aminocyclopropane-1-carboxylic acid (1.00 g, 4.25 mmol) in DMF (10 mL), followed by the addition of DIPEA (137 g, 10.6 mmol) and HATU (1.80 g, 4.73 mmol). The reaction mixture was stirred at room temperature for 15 min, followed by the addition of NH4OH (4 mL). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated in vacuo. The yellow solid residue was dissolved in EtOAc/H2O. The organic phase was separated, washed with water, brine, dried over anhydrous Na2SO4, filtered, concentrated and dried under high vacuum to afford 935 mg of (1-carbamoyl-cyclopropyl)-carbamic acid benzyl ester as a light yellow solid, m/z 235.8 [M+1]+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe yellow solid residue was dissolved in EtOAc/H2O
  4. customThe organic phase was separated
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-42507af72f764fc89bca0ba90558eba8
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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