1,2-Dichloroethane → (2S,2S)-nicotinic acid 2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-(2-methoxycarbonylamino-3,3-diphenyl-propionylamino)-hexyl ester

HRID 132703

Reaktionsgleichung

Reaktionsgleichung von HRID 132703
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:17]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:7][O:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:53][O:54][C:55]([NH:57][C@@H:58]([CH:62]([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:59](O)=[O:60])=[O:56]>CN(C=O)C>[NH2:31][C:28]1[CH:27]=[CH:26][C:25]([S:22]([N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C@@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:59](=[O:60])[C@@H:58]([NH:57][C:55]([O:54][CH3:53])=[O:56])[CH:62]([C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH2:7][O:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=2)(=[O:24])=[O:23])=[CH:30][CH:29]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acidHCID 131726927(2S)-nicotinic acid 6-amino-2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-hexyl ester

Produkt 1

HCID 11721810(2S,2S)-nicotinic acid 2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-(2-methoxycarbonylamino-3,3-diphenyl-propionylamino)-hexyl esterAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product of step B, (2S)-nicotinic acid 6-amino-2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-hexyl ester (100 mg, 0.22 mmol) was dissolved in anhydrous DMF (2 mL) and treated with 0.062 mL (0.45 mmol) of triethylamine followed by EDC (100 mg, 0.56 mmol), HOBt (75 mg, 0.56 mmol) and (2S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid (56 mg, 0.19 mmol). The mixture was stirred overnight at room temperature. The product was extracted with ethyl acetate (40 mL) and water (40 mL). The organic layer was separated and dried with Na2SO4, then evaporated to give 160 mg of crude oil. The residue was purified by flash chromatography with a mixture of eluents hexane/ethyl acetate (2/8). The title compound was obtained as a clear oil in 20% yield (25 mg).

Aufarbeitung

  1. extractionThe product was extracted with ethyl acetate (40 mL) and water (40 mL)
  2. customThe organic layer was separated
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customto give 160 mg of crude oil
  6. customThe residue was purified by flash chromatography with a mixture of eluents hexane/ethyl acetate (2/8)

Quellen und Nachweise

ORD-Eintrag
ord-243b3a79396548279078ae79ee734d05
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388008B2

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