Triethylamine → HCID 86657585, compound

HRID 1040426Notes

Reaction equation

HRID 1040426 reaction equation
[C:1](NC1(C(O)=O)CC1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.CN(C(ON1[N:39]=[N:38][C:33]2[CH:34]=C[CH:36]=[N:37][C:32]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:47]([O:51][C:52](NN)=[O:53])([CH3:50])([CH3:49])[CH3:48].CC1C([O:63]C(C)=O)=CC(C(C)C)=C(OCC[NH+](C)C)C=1.[Cl-]>CN(C=O)C.O>[C:47]([O:51][C:52]([NH:39][NH:38][C:33]1([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:34][CH:32]1[N:37]=[C:36]=[O:63])=[O:53])([CH3:50])([CH3:49])[CH3:48]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 13758Moxisylyte hydrochlorideHCID 70091tert-Butyl carbazateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15686068HCID 15686068, compound

Product 1

HCID 86657585HCID 86657585, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzoylamino-cyclopropanecarboxylic acid (5.0 g, 21.3 mmol) in DMF (5 mL) was added Et3N (2.94 mL, 21.3 mmol) and HATU (8.08 g, 21.3 mmol). The reaction mixture was allowed to stir for 10 min then hydrazinecarboxylic acid tert-butyl ester (2.81 g, 21.3 mmol) was added. The reaction was allowed to stir at room temperature overnight. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined extracts were washed with saturated NaHCO3, 2N HCl, brine and dried with MgSO4. The mixture was filtered, concentrated in vacuo, and purified by silica gel chromatography (25-100% EtOAc in hexanes) to give the N′-(1-benzyloxy-carbonylamino-cyclopropyl)-hydrazinecarboxylic acid tert-butyl ester (6.2 g, 17.7 mmol) as a white solid, m/z 250.6 [M−101]+.

Workup

  1. stirringto stir at room temperature overnight
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined extracts were washed with saturated NaHCO3, 2N HCl, brine
  4. dry with materialdried with MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (25-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-586980b88d01402ea2efb0e4950b4ec7
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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