1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (S)-tert-Butyl 1-oxo-1-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)butan-2-ylcarbamate

HRID 524977Notes

Reaction equation

[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8].[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH2:28][CH3:29])[C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].CCN=C=NCCCN(C)C.Cl>C1COCC1.ClCCl>[O:26]=[C:25]([NH:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:8])[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@@H:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:28][CH3:29]

Participants

Conditions

Temperature: 55 °C

Procedure

2.0 g (9.94 mmol) of 1-amino-N-phenyl-1H-pyrrole-2-carboxamide, 2.45 g (12.05 mmol) of (S)-2-(tert-butoxycarbonylamino)butanoic acid (purchased from Aldrich®, cat. no. 15533) and 1.90 g (12.24 mmol) of EDC.HCl were dissolved in a mixture of 90 mL of THF and 30 mL of dichloromethane. The resulting solution was heated at 55° C. overnight. Then the solvents were evaporated and the crude residue was taken up in dichloromethane and washed with an aqueous solution of sodium bicarbonate and brine. The organic layer was dried over magnesium sulphate, filtered and the solvent was evaporated. The solid obtained was triturated in diethyl ether to furnish 2.47 g (64% yield) of the title compound.

Workup

customThen the solvents were evaporated
washwashed with an aqueous solution of sodium bicarbonate and brine
dry with materialThe organic layer was dried over magnesium sulphate
filtrationfiltered
customthe solvent was evaporated
customThe solid obtained
customwas triturated in diethyl ether

Sources & evidence

ORD record: ord-8739faf1b291408aa0863866a5ac7cb1
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340547B2

Reaction notes

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