Hydrochloric Acid → tert-Butyl (3S)-3-[((3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-ylamino)-carbonyl]piperidine-1-carboxylate

HRID 2065472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2065472
[Cl:1][C:2]1[C:3]([CH3:25])=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18](=[O:24])OC(C)(C)C)[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[C:61]([O:65][C:66]([N:68]1[CH2:73][CH2:72][CH2:71][C@H:70](C(O)=O)[CH2:69]1)=[O:67])([CH3:64])([CH3:63])[CH3:62]>O1CCOCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([CH3:25])=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18]([C@H:72]3[CH2:71][CH2:70][CH2:69][N:68]([C:66]([O:65][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:67])[CH2:73]3)=[O:24])[CH2:12]2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6951168(3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 86602353tert-butyl {(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}carbamate

Produkt 1

HCID 58656262tert-Butyl (3S)-3-[((3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-ylamino)-carbonyl]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

tert-Butyl {(3S)-1-[(3-chloro-2-methylphenyl)sulfonyl]piperidin-3-yl}carbamate (58.34 mg, 0.0001500 mol) was treated with 4.0 M of hydrogen chloride in 1,4-dioxane (1.0 mL) at rt for 30 min. The solvent was evaporated under reduced pressure and the residue was dissolved in DMF (1.0 mL) and to this was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (69.6 mg, 0.000157 mol), 4-methylmorpholine (100.0 uL, 0.0009096 mol), and (3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (34.4 mg, 0.000150 mol) at rt. After stirring for 1 h, the reaction mixture was diluted with ethyl acetate (5 mL) and washed with NaHCO3 (7.5%, 3×2 mL) and brine (3×20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product which was used directly in the next step without further purification.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (1.0 mL)
  3. washwashed with NaHCO3 (7.5%, 3×2 mL) and brine (3×20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a550b4fdc9944c908cf4b53ce86a0faf
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288417B2

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