Diisopropylethylamine → HCID 178454607、化合物

HRID 333412ノート

反応式

HRID 333412 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.[C:63]([O:68][C:69]1([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[CH2:72][NH:71][CH2:70]1)(=[O:67])[CH2:64][CH2:65][CH3:66]>ClCCl.CN(C)C=O>[C:63]([O:68][C:69]1([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[CH2:70][N:71]([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)[CH2:72]1)(=[O:67])[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 669880793-Phenylazetidin-3-yl butyrate trifluoroacetateHCID 178490381HCID 178490381、化合物

生成物 1

HCID 178454607HCID 178454607、化合物収率 4.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To 80 mg (0.24 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)-propanoic acid (cf. preparation 2-3) dissolved in 2.75 mL of dichloromethane and 1.25 mL of dimethylformamide are added 0.08 mL (0.48 mmol) of diisopropylethylamine, 84 mg (0.26 mmol) of TBTU and 88 mg (0.26 mmol) of 3-phenylazetidin-3-yl butyrate trifluoroacetate. After 2 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 chromatographed by preparative TLC (eluent: 9/1 dichloromethane/methanol). 5.4 mg of 1-[2-{3-[2-(1H-imidazol-4-yl)ethyl]-ureido}-3-(4-methoxyphenyl)propionyl]-3-phenylazetidin-3-yl butyrate are obtained in a yield of 2%.

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 chromatographed by preparative TLC (eluent: 9/1 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-49f8addc701a48ea854b72307d0fc303
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…