Acetic Acid → (2S,5R)-4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627257
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[C:11]([CH2:21][CH2:22][N+:23]([O-])=O)=[CH:12][C@H:13]2[C:18]([NH2:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](O)(=[O:28])[CH3:27].CCN(C(C)C)C(C)C.C(OC(=O)C)(=O)C>C(O)C.C(Cl)Cl.[Zn]>[C:26]([NH:23][CH2:22][CH2:21][C:11]1[C@@H:10]2[CH2:17][N:14]([C:15](=[O:16])[N:9]2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:13]([C:18]([NH2:20])=[O:19])[CH:12]=1)(=[O:28])[CH3:27]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 89853135(2S,5R)-6-(benzyloxy)-4-(2-nitroethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide2×

Produkt 1

HCID 89863102(2S,5R)-4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2S,5R)-6-(benzyloxy)-4-(2-nitroethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (Intermediate 226, 0.300 g, 0.87 mmol) in ethanol (10 mL) was added zinc dust (1.416 g, 21.66 mmol) and acetic acid (1.984 mL, 34.65 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. Then DIPEA (2.118 mL, 12.13 mmol) was added to reaction mixture followed by acetic anhydride (0.245 mL, 2.60 mmol). The reaction mixture was stirred for an additional 2 hours, then diluted with DCM, washed with saturated bicarbonate and concentrated to dryness. Flash chromatography, 0%-10% MeOH/DCM, afforded the title compound as a clear oil (0.31 g, 61%).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for an additional 2 hours
  2. washwashed with saturated bicarbonate
  3. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8111aa82e42d4b2bab1158e5e0716f91
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

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