Triethylamine → HCID 178501129, compound

HRID 538067Notes

Reaction equation

HRID 538067 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]([OH:25])=O)([O-:15])=[O:14].Cl.[CH3:27][O:28][C:29]([CH:31]1[CH2:36][CH2:35][CH:34]([CH2:37][NH2:38])[CH2:33][CH2:32]1)=[O:30].C(N(CC)CC)C>C(OCC)(=O)C.CC(C)=O.C(Cl)Cl>[CH3:27][O:28][C:29]([C@H:31]1[CH2:36][CH2:35][C@H:34]([CH2:37][NH:38][C:23](=[O:25])[CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N+:13]([O-:15])=[O:14])[CH2:33][CH2:32]1)=[O:30]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 77337(2-Nitrophenyl)acetic acidHCID 12721445Methyl trans-4-(Aminomethyl)cyclohexanecarboxylate Hydrochloride

Product 1

HCID 178501129HCID 178501129, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

CDI (27.6 mmol, 4.47 g) was added portion wise to a stirring solution of o-nitrophenyl acetic acid (27.6 mmol, 5.00 g) in ethyl acetate (20 mL) at room temperature. The mixture was left stirring for 1 h and then was sequentially added of a solution of 4-Aminomethyl-cyclohexanecarboxylic acid methyl ester hydrogen chloride salt in ethyl acetate (20 mL), triethyl amine (72.5 mmol, 10 mL), DCM (5 mL) and acetone (5 mL). The final mixture was stirred at room temperature overnight. The reaction mixture was filtered through a paper filter, the filtered solution was washed with a (1N) NaOH (2×15 mL) and then with brine, the organic phase was dried over anhydrous Na2SO4, the solvent was removed under reduced pressure to obtain the titled compound. (8.2 g, 90%).

Workup

  1. waitThe mixture was left
  2. filtrationThe reaction mixture was filtered through a paper
  3. filtrationfilter
  4. washthe filtered solution was washed with a (1N) NaOH (2×15 mL)
  5. dry with materialwith brine, the organic phase was dried over anhydrous Na2SO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-96e0772af2eb48d3ba6941a5a1e5da36
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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