Hydrochloric Acid → HCID 54437783, compound

HRID 1374985Notes

Reaction equation

[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17](=[O:34])[C@H:18]([NH:29][C:30](=[O:33])[CH2:31]Cl)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([O:27][CH3:28])[CH:21]=1.Cl>CN(C)C=O.ClCCl>[CH3:15][O:16][C:17](=[O:34])[C@H:18]([NH:29][C:30](=[O:33])[CH2:31][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([O:27][CH3:28])[CH:21]=1

Participants

Conditions

Temperature: 35 °C

Procedure

Benzylamine (1.65 g) and potassium carbonate (1.28 g) were added successively to a solution of (2R)-2-[N-(chloroacetyl)amino]-3-(3-methoxy-4-methylphenyl)propionic acid methyl ester (1.85 g) in N,N-dimethylformamide (15 ml) at 20° C. After being stirred at 35° C. for 1.5 hours, the mixture was poured into a mixture of ice-water (20 ml) and dichloromethane (20 ml). After the mixture was adjusted to pH 9 with diluted aqueous hydrochloric acid under stirring, the organic layer was separated, washed with brine (20 ml), dried over magnesium sulfate and evaporated under reduced pressure to give an oil of (2R)-2-[N-(benzylaminoacetyl)-amino]-3-(3-methoxy-4-methylphenyl)propionic acid methyl ester. A solution of (2R)-2-[N-(benzylaminoacetyl)amino]-3-(3-methoxy-4-methylphenyl)propionic acid methyl ester obtained by above procedure and acetic acid (0.18 ml) in isopropyl alcohol (10 ml) was stirred for 12 hours under reflux.

Workup

stirringunder stirring
customthe organic layer was separated
washwashed with brine (20 ml)
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-2780cb9309fa430c996dc542320aff99
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166598B2

Reaction notes

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