Dimethylacetamide → {2-[(S)-2-(2-Benzyl-2H-tetrazol-5-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

HRID 222510

Reaktionsgleichung

Reaktionsgleichung von HRID 222510
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=N[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2[N:51](O)[N:50]=[N:49][C:47]=2C=1.[CH:53]([N:56]([CH:59]([CH3:61])[CH3:60])CC)([CH3:55])C.CC([N:65](C)C)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10]([N:56]1[CH2:53][CH2:55][CH2:61][C@H:59]1[C:60]1[N:51]=[N:50][N:49]([CH2:47][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:65]=1)=[O:12])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 5

HCID 31374DimethylacetamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7004938N-(tert-Butoxycarbonyl)-L-cyclohexylglycine

Produkt 1

HCID 59787961{2-[(S)-2-(2-Benzyl-2H-tetrazol-5-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butoxycarbonylamino-cyclohexyl-acetic acid (123.8 mg, 0.48 mmol) in DMA (5 mL) is added HBTU (248.8 mg, 0.656 mmol), HOBt (88.6 mg, 0.656 mmol) and diisopropylethylamine (305 uL, 1.75 mmol). The mixture is stirred at room temperature for 5 minutes. A solution of compound D in DCM (5 mL) is added to the above mixture at 0° C. The reaction mixture is stirred at room temperature for 1 hour and concentrated under vacuum. The residue is diluted with EtOAc. The organic is washed with brine, citric acid (5%), brine, NaHCO3 (Sat.) and brine. The organic layer is then dried and concentrated under vacuum. The residue is purified by flash column chromatography (Hexanes/EtOAc) to provide the title compound 190 mg (92%). M+H+=369.

Aufarbeitung

  1. stirringThe reaction mixture is stirred at room temperature for 1 hour
  2. concentrationconcentrated under vacuum
  3. additionThe residue is diluted with EtOAc
  4. washThe organic is washed with brine, citric acid (5%), brine, NaHCO3 (Sat.) and brine
  5. customThe organic layer is then dried
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by flash column chromatography (Hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-7709b56c7bfe46e192362c88c5d88a45
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207183B2

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