Triethylamine → HCID 13241884, compound

HRID 1733666Notes

Reaction equation

HRID 1733666 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:26][CH2:25][CH2:24][C@H:12]1[C:13]([NH:15][C@H:16]([C:21]([OH:23])=O)[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:28]([O:30][C:31](=[O:34])[CH2:32][NH2:33])[CH3:29].C(N(CC)CC)C.C1(C)C=CC(S(ON2C3C=C([N+]([O-])=O)C=CC=3N=N2)(=O)=O)=CC=1>C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[CH2:28]([O:30][C:31](=[O:34])[CH2:32][NH:33][C:21](=[O:23])[C@H:16]([CH2:17][CH:18]([CH3:19])[CH3:20])[NH:15][C:13](=[O:14])[C@@H:12]1[CH2:24][CH2:25][CH2:26][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:29]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 2818243HCID 2818243, compoundHCID 20300013HCID 20300013, compound

Product 1

HCID 13241884HCID 13241884, compoundYield 52.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(N-Benzyloxycarbonyl-L-prolyl)-L-leucine (4.6 g), glycine ethyl ester hydrochloride (1.8 g) and triethylamine (1.78 ml) are dissolved in dry chloroform (40 ml) and thereto is added 1-(p-toluenesulfonyloxy)-6-nitro-1,2,3-benzotriazole (4.25 g) under ice-cooling and the mixture is stirred for 1 hour. After allowing to stand overnight, to the mixture are added water and ethyl acetate. The ethyl acetate layer is washed with 1 N aqueous ammonia containing 5% NaCl (six times), water, 1 N hydrochloric acid and water in order, dried over anhydrous magnesium sulfate, and then the solvent is distilled off. The resulting residue is washed with ether-petroleum ether to give N-[N-(N-benzyloxycarbonyl-L-prolyl)-L-leucyl]glycine ethyl ester (3.0 g), melting point: 149°-150° C.

Workup

  1. temperaturecooling
  2. waitto stand overnight, to the mixture
  3. washThe ethyl acetate layer is washed with 1 N aqueous ammonia containing 5% NaCl (six times), water, 1 N hydrochloric acid and water in order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off
  6. washThe resulting residue is washed with ether-petroleum ether

Sources & evidence

ORD record
ord-5e3a359d08d14f76aa0628f0516b6cd5
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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