Lithium Hydroxide → benzyl (2S)-2-amino-3-methylbutanoate

HRID 1067058

反応式

HRID 1067058 の反応式
C(OC(=O)CCC=C)(=O)CCC=C.[Li+].[OH-].[CH2:16]([O:23][C:24](=[O:47])[C@H:25]([CH:44]([CH3:46])[CH3:45])[NH:26]C(=O)C(NC(OCC1C=CC=CC=1)=O)CC=C)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1[C@H](N2C(=O)N=C(N)C=C2)O[C@H](COP(O)(O)=O)[C@H]1OP(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(O)=O>CN(C=O)C.C1COCC1>[CH2:16]([O:23][C:24](=[O:47])[C@H:25]([CH:44]([CH3:45])[CH3:46])[NH2:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 3939Lithium HydroxideHCID 1955115'-Phospho-2'-deoxyribocytidylylriboadenosineHCID 27334394-Pentenoic anhydrideHCID 20662988N-(N-benzyloxycarbonyl-2-amino-4-Pentenoyl)-L-valine benzyl ester

生成物 1

HCID 6950584benzyl (2S)-2-amino-3-methylbutanoate収率 94%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

N-(4-pentenoyl)valyl-pdCpA was prepared. Treatment of S-valine methyl ester with 4-pentenoic anhydride afforded the respective amide as a colorless oil in 73% yield. Following hydrolysis of the ester moiety (LiOH, aq THF), the derived intermediate was converted to the respective cyanomethyl ester (4). Admixture of 4 and pdCpA Robertson, et al., Nucleic Acids Res. 17:9649 (1989), in freshly distilled DMF afforded N-(4-pentenoyl)valyl-pdCpA (5) as a colorless solid in 94% yield. A sample of N-(2-nitroveratryloxycarbonyl)valyl-pdCpA was prepared as described, Robertson, et al., J. Am. Chem. Soc. 113:2722 (1991) for comparative purposes.

出典と根拠

ORDレコード
ord-b9b01da9b23a47ad8e081d38b9ec2dc2
出典データセット
uspto-grants-2001_06
特許番号
US06245938B1

関連ノート

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