N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-alanine → alpha-L-aspartyl-D-alanine-(R)-alpha-methoxymethylbenzylamide

HRID 778

Reaction equation

HRID 778 reaction equation
C(OC([NH:11][C@H:12]([C:24]([NH:26][C@@H:27]([C:29](O)=[O:30])[CH3:28])=[O:25])[CH:13](CC1C=CC=CC=1)[C:14](=[O:16])[OH:15])=O)C1C=CC=CC=1.Cl.[CH3:33][O:34][CH2:35][C@H:36]([NH2:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH3:33][O:34][CH2:35][C@H:36]([NH:43][C:29](=[O:30])[C@@H:27]([CH3:28])[NH:26][C:24](=[O:25])[C@H:12]([CH2:13][C:14](=[O:15])[OH:16])[NH2:11])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 53966575N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-alanineHCID 66589172(R)-2-Methoxy-1-phenylethanamine hydrochloride

Product 1

HCID 22882906alpha-L-aspartyl-D-alanine-(R)-alpha-methoxymethylbenzylamideYield 57.3%

Procedure

The same process as in Example 15 was repeated, except that N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-alanine was used in place of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-valine and that (R)-α-methoxymethylbenzylamine hydrochloride was used in place of (R)-α-ethoxymethyl benzylamine hydrochloride, and α-L-aspartyl-D-alanine-(R)-α-methoxymethylbenzylamide was obtained as a solid product. The total yield was 57.3%.

Sources & evidence

ORD record
ord-12a035e31d384b0d952ee7e106393c5e
Source dataset
uspto-grants-1998_03
Patent number
US05723165

Linked notes

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