Diisopropylethylamine → HCID 178450015、化合物

HRID 333413ノート

反応式

HRID 333413 の反応式
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:24])[NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[N:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.FC(F)(F)C(O)=O.[CH2:63]([O:67][C:68]1([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[CH2:71][NH:70][CH2:69]1)[CH2:64][CH2:65][CH3:66]>ClCCl.CN(C)C=O>[CH2:63]([O:67][C:68]1([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[CH2:71][N:70]([C:12](=[O:14])[CH:11]([NH:10][C:9]([NH:8][CH2:7][CH2:6][C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)=[O:24])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:69]1)[CH2:64][CH2:65][CH3:66]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 669880053-Butoxy-3-phenylazetidine trifluoroacetateHCID 178490381HCID 178490381、化合物

生成物 1

HCID 178450015HCID 178450015、化合物収率 3.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To 57 mg (0.17 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)-propanoic acid (cf. preparation 2-3) dissolved in 4 mL of dichloromethane and 1.5 mL of dimethylformamide are added 0.12 mL (0.68 mmol) of diisopropylethylamine, 61 mg (0.19 mmol) of TBTU and 55 mg (0.17 mmol) of 3-butoxy-3-phenylazetidine trifluoroacetate. After 3 hours, the solution is washed with 1N sodium hydroxide solution and the organic products are extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product obtained is purified by preparative TLC (eluent: 9/1 dichloromethane/methanol). 3 mg of 1-[2-(3-butoxy-3-phenylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]-3-[2-(1H-imidazol-4-yl)ethyl]urea are obtained in a yield of 3%.

後処理

  1. washthe solution is washed with 1N sodium hydroxide solution
  2. extractionthe organic products are extracted with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customis purified by preparative TLC (eluent: 9/1 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-afab8191d9de4c83a9c281e628888260
出典データセット
uspto-grants-2014_11
特許番号
US08877968B2

反応ノート

読み込み中…