Benzylamine → HCID 18638658, compound

HRID 2073591Notes

Reaction equation

HRID 2073591 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]([OH:27])=O)[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C.CCOCC>[CH2:28]([NH:35][C:25](=[O:27])[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 98765IN2-(benzyloxycarbonyl)-N6-(tert-butoxycarbonyl)-L-lysineHCID 178418300HCID 178418300, compound

Product 1

HCID 18638658HCID 18638658, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

5 g (13.14 mmol) of Nα-benzyloxycarbonyl-Nε-tert.-butoxycarbonyl-L-lysine in 30 cm3 of dry DMF and 1.41 g (13.14 mmol) of benzylamine are condensed in the presence of 2.01 g (13.14 mmol) of hydroxybenzotriazole in 10 cm3 of dry DMF and 2.98 g (14.54 mmol) of dicyclohexylcarbodiimide in 10 cm3 of dry DMF. A pasty solid is obtained after treatment under the same conditions as for the preparation of the compound (5). This solid is covered with ether to give a precipitate of N-benzyl-Nα-benzyloxycarbonyl-Nε-tert.-butoxycarbonyl-L-lysinamide (5.51 g; 89%).

Workup

  1. customA pasty solid is obtained after treatment under the same conditions

Sources & evidence

ORD record
ord-0c19060f2eb043b3a34ea61ceb8d6a34
Source dataset
uspto-grants-1990_04
Patent number
US04918105

Reaction notes

Loading…