Triethylamine → HCID 178513954, compound

HRID 470694Notes

Reaction equation

HRID 470694 reaction equation
C([N:3](CC)CC)C.[CH2:8]([O:15][C:16]([NH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([C:25]([OH:27])=O)[CH2:21][CH2:20]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[C:25]([C@H:22]1[CH2:23][CH2:24][C@H:19]([NH:18][C:16](=[O:17])[O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:20][CH2:21]1)(=[O:27])[NH2:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178523781HCID 178523781, compound

Product 1

HCID 178513954HCID 178513954, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (1.4 ml, 10.1 mmol) was added to an N,N-dimethylformamide (120 ml) solution of trans-4-{[(benzyloxy)carbonyl]amino}cyclohexanecarboxylic acid (1.40 g, 5.10 mmol), ammonium chloride (0.54 g, 10.1 mmol), 1-hydroxybenzotriazole (0.39 g, 2.50 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.35 g, 7.10 mmol) and the resulting mixture was stirred at room temperature for 19 hours. Water was added and the precipitated solid was collected by filtration to give 1.20 g (86%) of the title compound as a colorless solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-76da7bab9a4d406383af5eb142564b07
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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