Hydrazine hydrate (1:1) → HCID 178514428, compound

HRID 470692Notes

Reaction equation

HRID 470692 reaction equation
O.NN.O[N:5]1C2C=CC=CC=2N=[N:6]1.Cl.C(N=C=NCCCN(C)C)C.[C:26]([NH:36][C@H:37]1[CH2:42][CH2:41][C@H:40]([C:43]([OH:45])=O)[CH2:39][CH2:38]1)([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>O.CN(C)C=O>[NH:5]([C:43]([C@H:40]1[CH2:41][CH2:42][C@H:37]([NH:36][C:26](=[O:27])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:38][CH2:39]1)=[O:45])[NH2:6]

Participants

7

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178523781HCID 178523781, compound

Product 1

HCID 178514428HCID 178514428, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Hydrazine monohydrate (1.42 ml, 23.4 mmol), 1-hydroxybenzotriazole (2.44 g, 18.0 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.49 g, 23.4 mmol) were added to an N,N-dimethylformamide (75 ml) solution of trans-4-(carbobenzoxyamino)cyclohexanecarboxylic acid (5.00 g, 18.0 mmol) at room temperature and the resulting mixture was stirred for 3 days. Water (150 ml) was added to the reaction mixture and the precipitated solid was collected by filtration and dried under reduced pressure to give 4.52 g (86%) of the title compound as a colorless solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-2bbea0681f894194804b74e878d3a01d
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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