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 222512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222512
[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-87d94b5b4f5a4192aea6195f6e450a42
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207183B2

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