Triethylamine → Tert-butyl(1s,2r)-1-benzyl-2-hydroxy-3-{isobutyl[(4-vinylphenyl)sulfonyl]amino}propylcarbamate

HRID 243586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243586
[CH2:1]([C@H:8]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:9]([OH:16])[CH2:10][NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:30][CH3:31])CC)C.C([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[S:40](Cl)(=[O:42])=[O:41])=C>ClCCl>[CH2:1]([C@H:8]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[C@H:9]([OH:16])[CH2:10][N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[S:40]([C:35]1[CH:36]=[CH:37][C:38]([CH:30]=[CH2:31])=[CH:39][CH:34]=1)(=[O:42])=[O:41])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9902339tert-Butyl ((2S,3R)-3-hydroxy-4-((2-methylpropyl)amino)-1-phenylbutan-2-yl)carbamateHCID 21983175Vinylbenzenesulfonyl chloride

Produkt 1

HCID 91062328Tert-butyl(1s,2r)-1-benzyl-2-hydroxy-3-{isobutyl[(4-vinylphenyl)sulfonyl]amino}propylcarbamateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Example 1 (11.86 g) in dichloromethane (100 mL) was added triethylamine (TEA) (19.6 mL, 4 equivalents) followed by dropwise addition of vinylbenzenesulfonyl chloride (8.36 g, 1.2 equivalents) at 25° C. for 3 hrs. The mixture was partitioned in 1N sodium bicarbonate (NaHCO3) and ethyl acetate (EtOAc). The organic extract was concentrated, and the residue was chromatographed on silica gel, eluting with ethyl acetate/hexanes (1:4) to afford the title compound (9.6 g, 54%). 1H NMR (300 MHz, CDCl3): δ ppm 0.87 (d, J=6.44 Hz, 3H), 0.90 (d, J=6.78 Hz, 3H), 1.34 (s, 9H), 1.86 (m, 1H), 2.84 (dd, J=13.39, 6.61 Hz, 2H), 2.97 (m, 3H), 3.11 (m, 3H), 3.79 (s, 1H), 4.61 (s, 1H), 5.44 (d, J=10.85 Hz, 1H), 5.88 (d, J=17.63 Hz, 1H), 6.75 (dd, J=17.63, 10.85 Hz, 1H), 7.25 (m, 5H), 7.51 (d, J=8.48 Hz, 2H), 7.72 (d, J=8.48 Hz, 2H).

Aufarbeitung

  1. customThe mixture was partitioned in 1N sodium bicarbonate (NaHCO3)
  2. extractionThe organic extract
  3. concentrationwas concentrated
  4. customthe residue was chromatographed on silica gel
  5. washeluting with ethyl acetate/hexanes (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-5cdb2b8d525c4e1095f3901836b70280
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653141B2

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