Triethylamine → HCID 11337051, compound

HRID 1733665Notes

Reaction equation

HRID 1733665 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20][O:21][C:22](=[O:27])[C@H:23]([CH2:25][OH:26])[NH2:24].C(N(CC)CC)C.ClC1C=CC(S(ON2C3C=C(Cl)C=CC=3N=N2)(=O)=O)=CC=1>C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[CH3:20][O:21][C:22](=[O:27])[C@H:23]([CH2:25][OH:26])[NH:24][C:13](=[O:15])[C@@H:12]1[CH2:16][CH2:17][CH2:18][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]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole

Product 1

HCID 11337051HCID 11337051, compoundYield 79.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxycarbonyl-L-proline (1.25 g), L-serine methyl ester hydrochloride (0.78 g) and triethylamine (1.40 ml) are dissolved in dry chloroform (20 ml) and thereto is added 1-(p-chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole (1.72 g) under ice-cooling. After allowing to stand overnight, to the mixture are added water and ethyl acetate. The ethyl acetate layer is washed and dried, and then the solvent is distilled off to give N-(N-benzyloxycarbonyl-L-prolyl)-L-serine methyl ester (1.4 g), melting point: 96°-100° C.

Workup

  1. temperaturecooling
  2. washThe ethyl acetate layer is washed
  3. customdried
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-3cd8063d30fd4c84bc76418944d40333
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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