L-Tyrosine 1,1-dimethylethyl ester → N-(4-ethoxy-1-oxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl ester

HRID 1017508ノート

反応式

HRID 1017508 の反応式
C(O[C:4]1[C:8]([O:9][CH2:10][CH3:11])=[N:7][S:6](=[O:12])[N:5]=1)C.[C:13]([O:17][C:18](=[O:29])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[NH2:20])([CH3:16])([CH3:15])[CH3:14]>C(O)C>[C:13]([O:17][C:18](=[O:29])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[NH:20][C:4]1[C:8]([O:9][CH2:10][CH3:11])=[N:7][S:6](=[O:12])[N:5]=1)([CH3:16])([CH3:14])[CH3:15]

参加物

4

反応物 2

HCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 12927269Diethoxy-1,2,5-thiadiazol-1-one

生成物 1

HCID 53908618N-(4-ethoxy-1-oxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl ester収率 882.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 3,4-diethoxy-1-oxo-1,2,5-thiadiazole (1 g, 0.52 mmol) and L-tyrosine t-butyl ester (1.25 g, 0.52 mmol) in ethanol (25 mL) was stirred at room temperature for 60 hr. Solvent was removed under reduced pressure and the residue purified by flash column chromatography (silica, hexane:EtOAc 1:1 to give N-(4-ethoxy-1-oxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl ester (1.75 g, 88%). MS (+ESI, m/e) 382 (M+H)+.

後処理

  1. customSolvent was removed under reduced pressure
  2. customthe residue purified by flash column chromatography (silica, hexane:EtOAc 1:1

出典と根拠

ORDレコード
ord-fd3034675ef745cdb8c7c0040b6d6fb4
出典データセット
uspto-grants-2002_11
特許番号
US06479492B1

反応ノート

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