HCID 178453620, compound → HCID 178511258, compound

HRID 330437Notes

Reaction equation

HRID 330437 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:46])[C@H:9]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[C:41]([N+:42]([O-:44])=[O:43])=[CH:40][CH:39]=[C:38]([Cl:45])[CH:37]=3)=[CH:31][CH:30]=2)[NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][NH:20]C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[O:12])=[CH:3][CH:2]=1>[Cl-].O1CCOCC1>[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:46])[C@H:9]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[C:41]([N+:42]([O-:44])=[O:43])=[CH:40][CH:39]=[C:38]([Cl:45])[CH:37]=3)=[CH:31][CH:30]=2)[NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][NH2:20])[CH2:15][CH2:14]2)=[O:12])=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 178453620HCID 178453620, compound

Product 1

HCID 178511258HCID 178511258, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 86639075HCID 86639075, compoundSolvent

Procedure

To a solution of N-(t-butyloxycarbonyl)-4-hydroxy-L-phenylalanine 4-pyridylamide (5.35 g) in dimethyl sulfoxide (100 ml) was added oily sodium hydride (0.62 g), followed by stirring at room temperature for 30 minutes. Thereafter, 2,4-dichloronitrobenzene (2.88 g) was added and stirred at room temperature for 10 hours. After a conventional post-treatment, N-(t-butyloxycarbonyl)-4-(3-chloro-6-nitrophenoxy)-L-phenylalanine 4-pyridylamide dihydrochloride (6.66 g) was obtained. The above compound (I) (6.50 g) was allowed to react with 4N-hydrogen chloride/dioxane solution (50 ml) to obtain 4-(3-chloro-6-nitrophenoxy-L-phenylalanine 4-pyridylamide dihydrochloride, which was further allowed to react with trans-4-(t-butyloxycarbonyl)aminomethylcyclohexylcarboxylic acid mixed acid anhydride obtained in Example 5 to obtain N-[trans-4-(t-butyloxycarbonyl)aminomethylcyclohexylcarbonyl]-4-(3-chloro-6-nitrophenoxy)-L-phenylalanine 4-pyridylamide (II) (7.16 g). The above compound (II) (7.00 g) was allowed to react with 4N-hydrogenn chloride/dioxane solution (150 ml) to obtain N-(trans-4-aminomethylcyclohexylcarbonyl)-4-(3-chloro-6-nitrophenoxy)-L-phenylalanine 4-pyridylamide (6.06 g).

Sources & evidence

ORD record
ord-dd4a7183e4004e87a532de9db802aa06
Source dataset
uspto-grants-1990_01
Patent number
US04895842

Reaction notes

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