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

HRID 2196849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196849
[C:1]([O:5][C:6]([N:8]([CH3:15])[C@@H:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.[NH2:66][CH:67]([CH:87]1[CH2:92][CH2:91][CH2:90][CH2:89][CH2:88]1)[C:68]([N:70]1[CH2:74][CH2:73][CH2:72][C@H:71]1[C:75]1[N:76]=[N:77][N:78]([CH2:80][C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[N:79]=1)=[O:69]>CC(N(C)C)=O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[N:8]([C@H:9]([C:10](=[O:12])[NH:66][CH:67]([CH:87]1[CH2:88][CH2:89][CH2:90][CH2:91][CH2:92]1)[C:68]([N:70]1[CH2:74][CH2:73][CH2:72][C@H:71]1[C:75]1[N:76]=[N:77][N:78]([CH2:80][C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[N:79]=1)=[O:69])[CH2:13][CH3:14])[CH3:15])([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15689337(2S)-2-(((1,1-Dimethylethoxy)carbonyl)methylamino)butanoic acidHCID 866010842-amino-1-[(2S)-2-(2-benzyltetrazol-5-yl)pyrrolidin-1-yl]-2-cyclohexylethanone;2,2,2-trifluoroacetic acid

Produkt 1

HCID 59788068((S)-1-{2-[(S)-2-(2-Benzyl-2H-tetrazol-5-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethylcarbamoyl}-propyl)-methyl-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(tert-butoxycarbonyl-methyl-amino)-butyric acid (53.0 mg, 0.24 mmol) in DMA (2 mL) is added HBTU (125.0 mg, 0.33 mmol), HOBt (44.6 mg, 0.33 mmol) and diisopropylethylamine (192 uL, 1.1 mmol). The mixture is stirred at room temperature for 5 minutes. A solution of compound F in DCM (2 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 crude oil is used directly in the next step without further purification. M+H+=554.

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 crude oil is used directly in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-c7f05225e96248519b5c3dcd65489bca
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338440B2

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