Triethylamine → HCID 18671395, compound

HRID 1057487Notes

Reaction equation

HRID 1057487 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:37][C:38]1[C:43]([NH2:44])=[CH:42][CH:41]=[CH:40][N:39]=1>C(Cl)Cl>[NH2:44][C:43]1[C:38]([NH:37][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:10])=[N:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99562,3-DiaminopyridineHCID 211844-(((Benzyloxy)carbonyl)amino)butanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18671395HCID 18671395, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[(phenylmethoxy)carbonylamino]butanoic acid (1.1 eq) was dissolved in methylene chloride (0.2M) followed by the addition of 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCA) (1.2 eq) and triethylamine (1.5 eq). The mixture was stirred at room temperature under nitrogen for 30 mins, followed by addition of 2,3-diaminopyridine. The mixture was then stirred at room temperature for 48 hrs., quenched with saturated sodium carbonate and extracted with ether. The organic phase was concentrated in vacuo and chromatographed on silica gel. (10% MeOH/CH2Cl2). EI-MS m/z 329 (M+H)+.

Workup

  1. stirringThe mixture was then stirred at room temperature for 48 hrs
  2. custom, quenched with saturated sodium carbonate
  3. extractionextracted with ether
  4. concentrationThe organic phase was concentrated in vacuo
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-8011cae5c5c947b3aaf04a0678bb46b3
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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