1-Hydroxybenzotriazole → Nalpha-benzenesulfonyl-Nepsilon-benzyloxycarbonyl-L-lysyl-L-proline benzylester

HRID 1074016Notes

Reaction equation

HRID 1074016 reaction equation
C1(NC2CCCCC2)CCCCC1.[C:14]1([S:20]([NH:23][C@H:24]([C:40](O)=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.[CH2:44]([O:51][C:52](=[O:58])[C@@H:53]1[CH2:57][CH2:56][CH2:55][NH:54]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:44]([O:51][C:52](=[O:58])[C@@H:53]1[CH2:57][CH2:56][CH2:55][N:54]1[C:40](=[O:41])[C@H:24]([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[NH:23][S:20]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:22])=[O:21])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733413Proline benzyl ester hydrochlorideHCID 14858911HCID 14858911, compound

Product 1

HCID 14858878Nalpha-benzenesulfonyl-Nepsilon-benzyloxycarbonyl-L-lysyl-L-proline benzylester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Nα -benzenesulfonyl-Nε -benzyloxycarbonyl-L-lysine dicyclohexylamine (3.01 g, 5 mmole), proline benzylester hydrochloride (1.21 g, 5 mmole) and HOBT (0.68 g, 5 mmole) were dissolved in methylene chloride (30 ml) and WSC hydrochloride (0.96 g, 5 mmole) was added thereto at -30° C. The mixture was stirred for 2 hours at less than 0° C., and then overnight at room temperature, and methylene chloride (70 ml) was added to the solution. The solution was washed with 5% aqueous sodium bicarbonate (100 ml, twice), 5% aqueous citric acid (100 ml, twice) and water (100 ml) in the order given, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain Nα -benzenesulfonyl-Nε -benzyloxycarbonyl-L-lysyl-L-proline benzylester[(yield: 1.68 g. 55.3%).

Workup

  1. customat -30° C
  2. washThe solution was washed with 5% aqueous sodium bicarbonate (100 ml
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ee43b547761e47538f52045cd8dedaee
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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