Phenylalanine amide → N-(toluene-4-sulfonyl)-L-prolyl-L-phenylalanine amide

HRID 279714

反応式

HRID 279714 の反応式
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12]([OH:14])=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:19][C@H:20]([C:28]([NH2:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:1]1([CH3:18])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12]([NH:19][C@H:20]([C:28]([NH2:30])=[O:29])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:14])(=[O:8])=[O:9])=[CH:5][CH:6]=1

参加物

3

反応物 2

HCID 445694Phenylalanine amideHCID 691957(2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid

生成物 1

HCID 54382446N-(toluene-4-sulfonyl)-L-prolyl-L-phenylalanine amide

実験手順

N-(Toluene-4-sulfonyl)-L-proline was reacted with L-phenylalanine amide using the procedure described in Method 12 to yield N-(toluene-4-sulfonyl)-L-prolyl-L-phenylalanine amide. To a solution of NaH (60% mineral oil—prewashed with THF) in THF at 0° C. was added N-(toluene-4-sulfonyl)-L-prolyl-L-phenylalanine amide and the reaction was stirred at 0° C. for 45 minutes. Toluene-4-sulfonyl chloride was added and the reaction was stirred for 16 hours at room temperature. The reaction mixture was extracted with EtOAc (3×50 mL) and 0.2 N HCl (50 mL), and the combined organic layers were washed successively with sat. NaHCO3 (50 mL), and sat. NaCl (2×50 mL), dried over MgSO4, filtered, and concentrated to yield the title compound as an oil.

出典と根拠

ORDレコード
ord-67481f61b200442a879954aab9626e59
出典データセット
uspto-grants-2002_03
特許番号
US06362341B1

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