methyl L-prolinate hydrochloride → N-(N-(Phenylacetyl)-L-alaninyl]-L-proline Methyl Ester

HRID 2180854Notes

Reaction equation

HRID 2180854 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]([C:13]([OH:15])=O)[CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:17][O:18][C:19](=[O:25])[C@@H:20]1[CH2:24][CH2:23][CH2:22][NH:21]1>>[CH3:17][O:18][C:19](=[O:25])[C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:13](=[O:15])[C@H:11]([CH3:12])[NH:10][C:8](=[O:9])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 2733200methyl L-prolinate hydrochlorideHCID 7004640N-(Phenylacetyl)-L-alanine

Product 1

HCID 22895052N-(N-(Phenylacetyl)-L-alaninyl]-L-proline Methyl Ester

Procedure

Following General Procedure A and using N-(phenylacetyl)-L-alanine (from Example B1 above) and L-proline methyl ester hydrochloride (Bachem), the title compound was prepared as an oil. The reaction was monitored by tlc (Rf=0.12 in 50% EtOAc/hexanes).

Sources & evidence

ORD record
ord-53cba3e076b0424c9e6b75284faf1137
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

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