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1,2-Dichloroethane → 1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 900573
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Reaktionsgleichung

Reaktionsgleichung von HRID 900573
C([O:5][C:6](=O)[NH:7][CH:8]([CH3:33])[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:32])[NH:17][CH:18]1[CH2:22][C:21](=[O:23])[O:20][CH:19]1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.[NH2:51][C:52]1[CH:60]=[CH:59][C:55](C(O)=O)=[CH:54][C:53]=1[Cl:61].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH2:25]([O:24][CH:19]1[CH:18]([NH:17][C:16]([CH:12]2[CH2:13][CH2:14][CH2:15][N:11]2[C:9](=[O:10])[CH:8]([NH:7][C:6](=[O:5])[C:55]2[CH:59]=[CH:60][C:52]([NH2:51])=[C:53]([Cl:61])[CH:54]=2)[CH3:33])=[O:32])[CH2:22][C:21](=[O:23])[O:20]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
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Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 172114-Amino-3-chlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22977790{2-[2-(2-Benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-pyrrolidin-1-yl]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 229774991-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 1.899 g (3.99 mmol) sample of 75 in CH2Cl2 (20 ml) was treated with anhydrous TFA (5 ml) then stirred at room temperature under N2 for 1 hour and evaporated to dryness. The residue was repeatedly concentrated from CH2Cl2 (3×) then dried under vacuum. The resulting residue was dissolved in CH2Cl2 (20 ml), cooled to 0° C., then treated with DIEA (5.6 ml, 8 eq, 32.1 mmol), 4-amino-3-chloro-benzoic acid (0.910 g, 5.3 mmol), HOBT (0.824 g, 6.1 mmol), and EDC (1.197 g, 6.23 mmol). The resulting mixture was warmed to room temperature and stirred for 18 hours. The solvent was removed in vacuo and the residue dissolved in EtOAc then washed with distilled water (3×), 0.5N NaHSO4 (2×), saturated NaHCO3 (2×) and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give a residue that was purified by flash chromatography using CH2Cl2/MeOH (99/1 to 97/3%). The title compound was obtained as a white solid (1.221 g, 58% yield). 1H-NMR (500 MHz, CD3OD) δ 1.15 (d, 0.25H), 1.29-1.60 (m, 2.75H), 2.41-2.54 (m, 0.5H), 2.55-2.70 (m, 0.5H), 2.77 (dd, 0.5H), 3.03 (ddd, 0.5H), 3.59-3.75 (m, 1H), 3.75-3.98 (m, 1H), 4.26-5.01 (m, 5H), 5.41-5.57 (m, 1H), 5.60-5.76 (m, 0.5H), 6.70-6.92 (m, 0.5H), 7.15-7.48 (m, 5H), 7.48-7.68 (m, 1H), 7.68-7.88 (m, 1H), 8.15-8.34 (m, 1H). Analytical HPLC (cyano column) (mixture of 2 diastereomers) 14.44, 14.89 min. LC-MS (ES+) m/e=529.3 (M+H).

Aufarbeitung

  1. customevaporated to dryness
  2. concentrationThe residue was repeatedly concentrated from CH2Cl2 (3×)
  3. customthen dried under vacuum
  4. dissolutionThe resulting residue was dissolved in CH2Cl2 (20 ml)
  5. temperaturecooled to 0° C.
  6. temperatureThe resulting mixture was warmed to room temperature
  7. stirringstirred for 18 hours
  8. customThe solvent was removed in vacuo
  9. dissolutionthe residue dissolved in EtOAc
  10. washthen washed with distilled water (3×), 0.5N NaHSO4 (2×), saturated NaHCO3 (2×) and brine
  11. dry with materialThe organic layer was dried over Na2SO4
  12. filtrationfiltered
  13. customevaporated
  14. customto give a residue that
  15. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-196a2f48e4914727bc5d6df0efd2334f
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07358273B2

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