Hippuric Acid → 3-(N-benzoylglycyl)amino-1-(4-chlorobenzyl)pyrrolidine

HRID 279251

Reaktionsgleichung

[C:1]([NH:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.Cl.[NH2:27][CH:28]1[CH2:32][CH2:31][N:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[CH2:29]1.CCN(CC)CC>C(Cl)(Cl)Cl>[C:1]([NH:9][CH2:10][C:11]([NH:27][CH:28]1[CH2:32][CH2:31][N:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[CH2:29]1)=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

N-Benzoylglycine (9.9 mg, 0.055 mmol), 3-ethyl-1-{3-(dimethylaminopropyl}carbodiimide hydrochloride (EDCI) (10.5 mg) and 1-hydroxybenzotriazole hydrate (HOBt) (7.4 mg) were added to a solution of 3-amino-1-(4-chlorobenzyl)pyrrolidine dihydrochloride (14.2 mg, 0.050 mmol) and Et3N (15.2 mg) in CHCl3 (2.5 mL). The reaction mixture was stirred at 25° C. for 16 h, washed with 2 N aqueous NaOH (2 mL×2) and brine (1 mL). After filtration through a PTFE membrane filter, the solvent was removed under reduced pressure to afford 3-(N-benzoylglycyl)amino-1-(4-chlorobenzyl)pyrrolidine (compound No. 1) as a pale yellow oil (17.7 mg, 95%): The purity was determined by RPLC/MS (95%); ESI/MS m/e 372.0 (M++H, C20H22ClN3O2).

Aufarbeitung

washwashed with 2 N aqueous NaOH (2 mL×2) and brine (1 mL)
filtrationAfter filtration through a PTFE membrane
filtrationfilter
customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-5b806f9e008446319d2b05e6b0502893
Quelldatensatz: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06362177B1

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