Ethyl 3-aminopent-4-enoate → Ethyl 3-[[4-[[4-(aminoiminomethyl)naphthyl](phenylmethyl)-amino]-1,4-dioxobutyl]amino]-4-pentenoate

HRID 1941559Notes

Reaction equation

HRID 1941559 reaction equation
Cl.[NH2:2][N:3]=[CH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([NH:15][C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=O)=[CH:7][CH:6]=1.[NH2:23][CH:24]([CH:31]=[CH2:32])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[NH2:2][N:3]=[CH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([N:15]([CH2:4][C:5]2[CH:14]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:16](=[O:22])[CH2:17][CH2:18][C:19]([NH:23][CH:24]([CH:31]=[CH2:32])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:21])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 10057602Ethyl 3-aminopent-4-enoateHCID 700611654-[[4-(Aminoiminomethyl)naphthyl]amino]-4-oxobutanoic acid hydrochloride

Product 1

HCID 70064524Ethyl 3-[[4-[[4-(aminoiminomethyl)naphthyl](phenylmethyl)-amino]-1,4-dioxobutyl]amino]-4-pentenoate

Procedure

The title compound was prepared in the manner of Example 1 substituting 4-[[4-(aminoiminomethyl)naphthyl]amino]-4-oxobutanoic acid hydrochloride for 4-[[4-(aminoiminomethyl)-3-phenyl]amino]-4-oxobutanoic acid hydrochloride and using ethyl 3-amino-4-pentenoate. The product was purified by reverse phase HPLC using the conditions of Example 1 to afford the title compound. The product was verified by 13C NMR (CD3 OD) δ13.2, 30.5, 31.3, 39.0, 48.5, 60.4, 114.6, 120.3, 123.1, 123.9, 124.8, 126.6, 127.0, 128.0, 128.1, 130.3, 136.8, 137.4, 167.6, 171.0, 172.6, 173.0; Chemical Ionization Mass Spectrometry (MH+)=411

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-88474f8699914fc4a4f8d808118fb4c5
Source dataset
uspto-grants-1997_12
Patent number
US05703125

Reaction notes

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