Benzylamine → HCID 178454181, compound

HRID 1770317Notes

Reaction equation

HRID 1770317 reaction equation
Cl.[C:2]([NH:9][C@@H:10]([C:18]([OH:20])=O)[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:17])[NH2:16])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([NH:28][C:18](=[O:20])[C@@H:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:17])[NH2:16])[NH:9][C:2]([O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[O:3])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 178454193HCID 178454193, compound

Product 1

HCID 178454181HCID 178454181, compound

Procedure

N-Boc-D-Arginine hydrochloride (100 mg, 0.3 mmol) was coupled with benzylamine (40 uL, 0.4 mmol) using the mixed anhydride method described in Example 322 to give N-Boc-D-arginine benzylamide. The Boc group was removed by treatment with 4 M hydrochloric acid in dioxane for 1 h. The resulting D-arginine benzylamide was coupled to N-Boc-(N-methyl)phenylalanyl-lysyl(N-epsilon-Boc)-prolyl-{(2R)-2-amino-3-cyclohexylpropanoyl}-{(2S)-2-amino-3-cyclohexylpropanoyl}-OH, which was prepared as described in Example 322, using 1-(3-dimethyl-aminopropyl)-3-ethyl carbodiimide hydrochloride in dimethylformamide using the method described in Example 322. The crude product was deprotected with 50% trifluoroacetic acid in methylene chloride. The material thus obtained was purified by HPLC as described in Example 2 to give the title compound in 26% overall yield.

Sources & evidence

ORD record
ord-ae9fbdc2004b4741a1e5ffe8d12666e5
Source dataset
uspto-grants-1995_01
Patent number
US05386011

Reaction notes

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