1-Hydroxybenzotriazole → HCID 14858896, compound

HRID 1074003Notes

Reaction equation

HRID 1074003 reaction equation
C1(NC2CCCCC2)CCCCC1.[C:14]([O:18][C:19]([NH:21][C@H:22]([C:27]([OH:29])=O)[CH2:23][CH2:24][S:25][CH3:26])=[O:20])([CH3:17])([CH3:16])[CH3:15].Cl.[CH2:31]([O:38][C:39](=[O:45])[C@@H:40]1[CH2:44][CH2:43][CH2:42][NH:41]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C)C=O>[CH2:31]([O:38][C:39](=[O:45])[C@@H:40]1[CH2:44][CH2:43][CH2:42][N:41]1[C:27](=[O:29])[C@H:22]([CH2:23][CH2:24][S:25][CH3:26])[NH:21][C:19]([O:18][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:20])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 89856L-Methionine, N-[(1,1-dimethylethoxy)carbonyl]-, compd. with N-cyclohexylcyclohexanamine (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 14858896HCID 14858896, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-t-butyloxycarbonyl-L-methionine dicyclohexylamine salt (44.36 g, 103 mmole), L-proline benzylester hydrochloride (2490 g, 103 mmole) and HOBT (13.92 g, 103 mmole) were dissolved in methylene chloride (400 ml), and WSC hydrochloride (19.75 g, 103 mmole) were added thereto at -30C. The mixture was stirred for 2 hours at less than 0° C., N,N-dimethylformamide (100 ml) was added thereto, and stirred further overnight at room temperature. The solution was washed with 5% aqueous sodium bicarbonate (400 ml, twice), 5% aqueous citric acid (400 ml, twice) and water (400 ml) in the order given, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain N-t-butyloxycarbonyl-L-methionyl-L-proline benzylester (yield: 46.27 g, 100%)

Workup

  1. stirringstirred further overnight at room temperature
  2. washThe solution was washed with 5% aqueous sodium bicarbonate (400 ml
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4eedc17f517e45229b4135d26a464a29
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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