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

HRID 133552

Reaction equation

HRID 133552 reaction equation
[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.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.Cl.Cl.[NH2:39][CH:40]1[CH2:44][CH2:43][N:42]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=2)[CH2:41]1>C(N(CC)CC)C.C(Cl)(Cl)Cl>[C:1]([NH:9][CH2:10][C:11]([NH:39][CH:40]1[CH2:44][CH2:43][N:42]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=2)[CH2:41]1)=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 464Hippuric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 184261801-(4-Chlorobenzyl)pyrrolidin-3-amine dihydrochloride

Product 1

HCID 98424043-(N-benzoylglycyl)amino-1-(4-chlorobenzyl)pyrrolidineYield 95.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

N-Benzoylglycine (9.3 mg, 0.055 mmol), 3-ethyl-1-[3-(dimethylamino)propyl]carbodiimide hydrochloride (EDCI) (1.05 mg) and 1-hydroxybenzotriazole hydrate (HOBt) (7.4 mg) were added to a chloroform (2.5 mL) solution of 3-amino-1-(4-chlorobenzyl)pyrrolidine dihydrochloride (14.2 mg, 0.050 mmol) and triethylamine (15.2 mg). The resulting reaction mixture was stirred at 25° C. for 16 hours and then washed with a 2 M aqueous solution of NaOH (2 mL×2) and brine. After filtration through a PTFE membrane filter, the solvent was removed under reduced pressure to provide 3-(N-benzoylglycyl)amino-1-(4-chlorobenzyl)pyrrolidine (Compd. No. 1) as an off-white oil (17.7 mg, 95%). The purity was determined by RPLC/MS (95%). ESI/MS m/e 372.0 (M++H, C20H22ClN3O2).

Workup

  1. customThe resulting reaction mixture
  2. washwashed with a 2 M aqueous solution of NaOH (2 mL×2) and brine
  3. filtrationAfter filtration through a PTFE membrane
  4. filtrationfilter
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-72cd6b5d7b994755b2e85d03e19ae34e
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Linked notes

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