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

HRID 2297318Notes

Reaction equation

HRID 2297318 reaction equation
[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]

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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 (

Sources & evidence

ORD record
ord-f65a871fd37c4562b641b5070a515e6c
Source dataset
uspto-grants-2002_12
Patent number
US06489440B1

Reaction notes

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