Potassium Carbonate → HCID 54530255, 화합물

HRID 1060428

반응식

HRID 1060428 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 54530255HCID 54530255, 화합물수율 71.8%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5a4d1d64491645f8951bcf4cfd31dc5c
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521666B1

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