HCID 86760705, compound → HCID 68831662, compound

HRID 747703Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:13]=[CH:12][C:11]([C:14]([NH:16][C@@H:17]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32](=[NH:34])[NH2:33])[CH:27]=2)[CH2:18][C:19]([O:21]CC)=[O:20])=[O:15])=[CH:10][CH:9]=1>Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:9]=[CH:10][C:11]([C:14]([NH:16][C@@H:17]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32](=[NH:33])[NH2:34])[CH:27]=2)[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

120 mg (0.18 mmol) of ethyl (3R)-3-[(biphenyl-4-carbonyl)amino]-4-(3-amidinophenoxy)butyrate trifluoroacetate was dissolved in 5 ml of concentrated hydrochloric acid, and the solution was stirred at 60° C. for 19 hours. The solvent was evaporated, and the residue was treated by the reversed-phase high-performance liquid chromatography with silica gel, containing octadodecyl group chemically bonded thereto, as the filler. After the elution with a mixed solvent of water and acetonitrile containing 0.1% (v/v) of trifluoroacetic acid, the fraction of the intended product was freeze-dried to obtain the title compound.

Workup

customThe solvent was evaporated
additionthe residue was treated by the reversed-phase high-performance liquid chromatography with silica gel
additioncontaining octadodecyl group
washAfter the elution with a mixed solvent of water and acetonitrile containing 0.1% (v/v) of trifluoroacetic acid
customthe fraction of the intended product was freeze-dried

Sources & evidence

ORD record: ord-c9f3e970b08644f6996b6fb0b81874ff
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396844B1

Reaction notes

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