Diisopropylethylamine → (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-undecylsuccinamic acid tert-butyl ester

HRID 2297318

반응식

HRID 2297318 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][C:24]([OH:26])=[O:25])[C:20]([OH:22])=O)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN([P+](ON1N=NC2C=C[CH:43]=[CH:44][C:39]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[CH:54]1C=C2N=NN(O)C2=CC=1.O.C(N(CC)C(C)C)(C)C.[NH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH3:85]>CN(C)C=O.O.C(OCC)(=O)C>[C:44]([O:26][C:24](=[O:25])[CH2:23][C@H:19]([NH:18][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17])[C:20]([NH:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH3:85])=[O:22])([CH3:43])([CH3:39])[CH3:54]

참가 물질

9

반응물 5

HCID 81531DiisopropylethylamineHCID 81742UndecylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27960291-Hydroxybenzotriazole hydrateHCID 7019016Fmoc-L-aspartic acid

생성물 1

HCID 53649195(S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-undecylsuccinamic acid tert-butyl ester수율 83.1%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (S)-2-(9H-fluoren-9-ylmethoxycarbonyl-amino)succinic acid (150 mg, 0.36 mmol), BOP reagent (162 mg, 0.36 mmol) and HOBT hydrate (56 mg, 0.36 mmol) in N,N-dimethylformamide (0.2 ml) was added N,N-diisopropylethylamine (64 μl, 0.36 mmol). After being stirred for 30 min at room temperature, 1-aminoundecane (79 μl, 0.37 mmol) was added. The mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water and extracted with Et2O. The combined extracts were washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. Purification of the residue by silica gel column chromatography (using n-hexane:ethyl acetate =3:1 as an eluent ) gave (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-undecylsuccinamic acid tert-butyl ester (169 mg, 82% yield) as a colorless amorphous solid.

후처리

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. extractionextracted with Et2O
  3. washThe combined extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by silica gel column chromatography (

출처 및 근거

ORD 기록
ord-f65a871fd37c4562b641b5070a515e6c
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06489440B1

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