Benzylamine → N-(Boc-L-phenylalanyl)benzylamine
Reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([NH:16][C@H:17]([C:25](O)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>>[C:9]([NH:16][C@H:17]([C:25]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:26])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10]Participants
Procedure
In substantially the same manner as Working Example 2, benzylamine (3.53 g) was condensed with Boc-L-phenylalanine (7.96 g) to give N-(Boc-L-phenylalanyl)benzylamine (9.30 g) (yield 87%). The compound thus obtained (7.08 g) was dissolved in ethyl acetate (100 ml), to which was added 4N hydrochloric acid/ethyl acetate solution (80 ml, manufactured by Kokusan Chemical Works, Ltd.), and the mixture was left standing for a half hour at room temperature. The reaction mixture was treated with ethylether to give N-(L-phenylalanyl)benzylamine hydrochloride (3.51 g) (yield 60%). The compound thus obtained (0.96 g) was condensed, in substantially the same manner as Working Example 8, with monoethyl ester of (2S,3S)-N-methylaziridine-2,3-dicarboxylic acid (0.52 g) obtained in Working Example 42 to give the above-titled compound (Compound 91; 0.86 g) as white crystals (yield 71%).
Sources & evidence
- ORD record
- ord-f664efae8f9144429f9b244b61f61f7b
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05668128
Reaction notes
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