Triethylamine → HCID 18786983, compound

HRID 1107380Notes

Reaction equation

HRID 1107380 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.Cl.[CH2:18]([O:20][C:21](=[O:25])[CH2:22][NH:23][CH3:24])[CH3:19].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C1COCC1>[CH2:18]([O:20][C:21](=[O:25])[CH2:22][N:23]([CH3:24])[C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH3:19]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 64245232-(2-Methylphenyl)benzoic acid

Product 1

HCID 18786983HCID 18786983, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(methylphenyl)benzoic acid (3.09 g, 14.55 mmol), sarcosine ethyl ester hydrochloride salt (2.23 g, 14.55 mmol), DCC (3.0 g, 14.55 mmol), HOBT (1.97 g, 14.55 mmol) and Et3N (1.47 g, 14.55 mmol) in THF (50 mL) were stirred at ambient temperature for 48 hours. The reaction was evaporated and the residue dissolved in EtOAc. The EtOAc solution was washed with HCl (10%), saturated NaHCO3 and brine, and dried (MgSO4). The EtOAc solution was filtered through a plug of silica gel follwoed by a second filtration through a plug of neutral alumina. Evaporation of the solution gave N-methyl-N-[2-(methylphenyl)benzoyl]glycine ethyl ester (4.5 g); LRMS (M+H)+ =312.2.

Workup

  1. customThe reaction was evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe EtOAc solution was washed with HCl (10%), saturated NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationThe EtOAc solution was filtered through a plug of silica gel
  6. filtrationfollwoed by a second filtration through a plug of neutral alumina
  7. customEvaporation of the solution

Sources & evidence

ORD record
ord-48524b28e2ea471da652b0f89104bba1
Source dataset
uspto-grants-2000_05
Patent number
US06060462

Reaction notes

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