Diisopropylethylamine → HCID 178454607, 화합물

HRID 333412노트

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HRID 333412 반응식
[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]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 669880793-Phenylazetidin-3-yl butyrate trifluoroacetateHCID 178490381HCID 178490381, 화합물

생성물 1

HCID 178454607HCID 178454607, 화합물수율 4.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-49f8addc701a48ea854b72307d0fc303
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877968B2

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