DL-Phenylalanine, methyl ester → N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester
Reaction equation
O.C([O-])(=O)C.[Ca+2].C([O-])(=O)C.C([O-])(=O)C.[Na+].[CH2:16]([O:23][C:24]([NH:26][C@H:27]([C:32]([OH:34])=O)[CH2:28][C:29]([OH:31])=[O:30])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:35][O:36][C:37](=[O:47])[C@H:38]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[NH2:39].COC(=O)C(CC1C=CC=CC=1)N>O>[CH3:35][O:36][C:37](=[O:47])[C@H:38]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[NH:39][C:32](=[O:34])[C@H:27]([CH2:28][C:29](=[O:30])[OH:31])[NH:26][C:24]([O:23][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:25]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
The preparation of the immobilized enzyme and the reaction were conducted in the same manner as in Example 1 with the exception that: The quantity of Thermoase and that of the calcium acetate monohydrate were 9.0 g and 0.45 g respectively, the quantity of the 0.05 M sodium acetate buffer solution of pH 7.5 was 90 ml; the acrylic ester matrix carrier (Amberlite XAD-7, Trademark) was replaced with 16.6 g of another carrier of the similar class (Amberlite XAD-8, Trademark, containing about 150 wt.% of water on a dry basis; the quantity of N-benzyloxycarbonyl-L-aspartic acid was 2.14 g (8 m mol): L-phenylalanine methyl ester was replaced with 2.87 g (16 m mol) of DL-phenylalanine methyl ester; the quantity of the water saturated ethyl acetate solution was changed to 26 ml; and the reaction time was five fours. N-Benzyloxycarbonyl-L-aspartyl-L-phenylalanine methyl ester was obtained in the yield of 79.8%.
Workup
- customThe preparation of the immobilized enzyme
Sources & evidence
- ORD record
- ord-949b3636b8db411babdca52620009706
- Source dataset
- uspto-grants-1981_08
- Patent number
- US04284721
Reaction notes
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