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Potassium Carbonate → N-(tert-butoxycarbonyl)-3,4-bis(2,6-dichlorobenzyloxy)-L-phenylalanine methyl ester

HRID 24656
ノート
印刷プレビュー

反応式

HRID 24656 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH2:4]Cl.[CH3:11][O:12][C:13](=[O:32])[C@H:14]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([OH:31])[CH:25]=1)[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C.O>[CH3:11][O:12][C:13](=[O:32])[C@H:14]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:4][C:3]2[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=2[Cl:10])=[C:26]([O:31][CH2:4][C:3]2[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=2[Cl:10])[CH:25]=1)[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 748322,6-Dichlorobenzyl chlorideHCID 14889488(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoate

生成物 1

HCID 54530255N-(tert-butoxycarbonyl)-3,4-bis(2,6-dichlorobenzyloxy)-L-phenylalanine methyl ester収率 71.8%

試薬・触媒・溶媒 3

HCID 67553
Tetrabutylammonium Iodide
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

2,6-Dichlorobenzyl chloride (1.73 g) was added to a suspension of N-(tert-butoxycarbonyl)-3,4-dihydroxy-L-phenylalanine methyl ester (2.5 g), K2CO3 (2.22 g), and n-Bu4NI (0.297 g) in DMF (15 mL) at room temperature. The mixture was stirred overnight at room temperature, diluted with water and extracted with ether. The extract was dried (MgSO4) and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexanes/CH2Cl2/EtOAc, 5:5:1) to yield N-(tert-butoxycarbonyl)-3,4-bis(2,6-dichlorobenzyloxy)-L-phenylalanine methyl ester (2.0 g), ESMS: m/z 630 (MH+), N-(tert-butoxycarbonyl)-3-(2,6-dichlorobenzyloxy)-4-hydroxy-L-phenylalanine methyl ester (0.39 g), ESMS: m/z 470(MH+), and N-(tert-butoxycarbonyl)-4-(2,6-dichlorobenzyloxy)-3-hydroxy-L-phenylalanine methyl ester (0.45 g), ESMS: m/z 470 (MH+), respectively.

後処理

  1. extractionextracted with ether
  2. dry with materialThe extract was dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography (silica gel; eluent: hexanes/CH2Cl2/EtOAc, 5:5:1)

出典と根拠

ORDレコード
ord-8e727efff0af4a0187c6413082883345
出典データセット
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06855843B2

反応ノート

読み込み中…

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