Triethylamine → HCID 18930538, compound

HRID 1598912Notes

Reaction equation

HRID 1598912 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.Cl.[NH2:14][C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=1)[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19].C(N(CC)CC)C.Cl.[CH3:35][O:36][C:37](=[O:40])[CH2:38][NH2:39]>ClCCl.O>[CH3:35][O:36][C:37]([CH2:38][NH:39][C:2](=[O:4])[NH:14][C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=1)[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])=[O:40]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 122755Glycine methyl ester hydrochlorideHCID 18930598HCID 18930598, compound

Product 1

HCID 18930538HCID 18930538, compoundYield 214.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A suspension of triphosgene (2.5 g, 8.42 mmol) and allyl 3-aminobenzoate hydrochloride (4.0 g, 18.7 mmol) in dichloromethane (80 ml) is cooled to -20° C. and triethylamine (9.64 ml, 69.2 mmol) is added dropwise thereto. The mixture is strirred for 30 minutes. To the mixture is added glycine methyl ester hydrochloride (2.82 g, 22.44 mmol). Then, triethylamine (3.75 ml, 18.7 mmol) is added dropwise, followed by stirring at -20° C. for 2.5 hours. Ice-cooled water is added to the reaction solution and, after stirring, the aqueous layer is extracted twice with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to obtain the objective compound (5.27 g). Yield 96%.

Workup

  1. additionis added to the reaction solution
  2. stirringafter stirring
  3. extractionthe aqueous layer is extracted twice with ethyl acetate
  4. washThe organic layer is washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-567e7098002945a39bdc67828f0d0448
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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