Triethylamine → HCID 18343599, compound

HRID 988014Notes

Reaction equation

HRID 988014 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([OH:7])=O.Cl.[CH3:13][O:14][C:15](=[O:21])[C@H:16]([C@@H:18]([CH3:20])[OH:19])[NH2:17].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>ClCCl>[CH3:13][O:14][C:15](=[O:21])[C@H:16]([C@@H:18]([CH3:20])[OH:19])[NH:17][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:2]([CH3:1])[CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 103563,5-Dimethylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734893Methyl L-threoninate hydrochloride

Product 1

HCID 18343599HCID 18343599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.00 g (6.66 mmol/1 eq) of 3,5-dimethylbenzoic acid and 1.13 g (6.66 mmol/1 eq) of L-threonine methyl ester hydrochloride are suspended in 50 ml dichloromethane. At 0° C., 2.04 ml (14.7 mmol/2.2 eq) of triethylamine are added dropwise. After 10 minutes' stirring, 2.55 g (13.3 mmol/2 eq) of N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride (EDC) are added, and after a further 15 min 1-hydroxybenzotriazole (HOBt) is added. Stirring is carried out for twelve hours, the solution assuming room temperature. The organic phase is washed with 10 ml each of H2O, hydrochloric acid (2N), and NaHCO3 solution. After drying over magnesium sulfate, the solvent is removed in vacuo. 1.70 g (6.41 mmol/96%) of a white solid are obtained, which may, if desired, be recrystallised from absolute diethyl ether.

Workup

  1. stirringStirring
  2. waitis carried out for twelve hours
  3. customassuming room temperature
  4. washThe organic phase is washed with 10 ml each of H2O, hydrochloric acid (2N), and NaHCO3 solution
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solvent is removed in vacuo
  7. custom1.70 g (6.41 mmol/96%) of a white solid are obtained
  8. custombe recrystallised from absolute diethyl ether

Sources & evidence

ORD record
ord-638ab76f931b4e5f8c6c29694b3ae01a
Source dataset
uspto-grants-2003_10
Patent number
US06632954B2

Reaction notes

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