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

HRID 777

Reaction equation

HRID 777 reaction equation
C(OC([NH:11][C@H:12]([C:24]([NH:26][C@@H:27]([C:32](O)=[O:33])[C@@H:28]([CH2:30][CH3:31])[CH3:29])=[O:25])[CH:13](CC1C=CC=CC=1)[C:14](=[O:16])[OH:15])=O)C1C=CC=CC=1.Cl.[CH3:36][O:37][CH2:38][C@H:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH3:36][O:37][CH2:38][C@H:39]([NH:46][C:32](=[O:33])[C@@H:27]([C@@H:28]([CH2:30][CH3:31])[CH3:29])[NH:26][C:24](=[O:25])[C@H:12]([CH2:13][C:14](=[O:15])[OH:16])[NH2:11])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

3

Reactant 2

HCID 54543031N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-isoleucineHCID 66589172(R)-2-Methoxy-1-phenylethanamine hydrochloride

Product 1

HCID 53660612alpha-L-aspartyl-D-isoleucine (R)-alpha-methoxymethylbenzylamideYield 22.1%

Procedure

The same process as in Example 15 was repeated, except that N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine 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-ethoxymethylbenzylamine hydrochloride, and α-L-aspartyl-D-isoleucine (R)-α-methoxymethylbenzylamide was obtained as a solid product. The total yield was 22.1%.

Sources & evidence

ORD record
ord-f6a778234f084513ae50b4ca3b6875a0
Source dataset
uspto-grants-1998_03
Patent number
US05723165

Linked notes

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