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

HRID 1280944

Reaktionsgleichung

Reaktionsgleichung von HRID 1280944
[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.Cl.CN(CCCN=C=N)C.O.ON1C2C=CC=CC=2N=N1.Cl.Cl.[NH2:37][CH:38]1[CH2:42][CH2:41][N:40]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=2)[CH2:39]1>C(Cl)(Cl)Cl.CCN(CC)CC>[C:1]([NH:9][CH2:10][C:11]([NH:37][CH:38]1[CH2:42][CH2:41][N:40]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=2)[CH2:39]1)=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 464Hippuric AcidHCID 27960291-Hydroxybenzotriazole hydrateHCID 184261801-(4-Chlorobenzyl)pyrrolidin-3-amine dihydrochlorideHCID 21899179Dimethylaminopropyl carbodiimide hydrochloride

Produkt 1

HCID 98424043-(N-benzoylglycyl)amino-1-(4-chlorobenzyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

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

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

Quellen und Nachweise

ORD-Eintrag
ord-dcc9b4670f1e4ec1a467bc1e330e69da
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451842B1

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