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1-Hydroxybenzotriazole → (4S,7S,11aR)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic Acid

HRID 722733
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 722733
C(OC1C(NC([C@H]2N3C(=O)[C@@H](NC(=O)C4C=CC=CC=4)CC=CC[C@H]3CCC2)=O)CC(=O)O1)C.C(OC(=O)NC1CC(=O)OC1OCC)C=C.[C:51]([NH:59][C@@H:60]1[C:67](=[O:68])[N:66]2[C@H:69]([C:73]([OH:75])=[O:74])[CH2:70][CH2:71][CH2:72][C@H:65]2[CH2:64][CH:63]=[CH:62][CH2:61]1)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:51]([NH:59][C@@H:60]1[C:67](=[O:68])[N:66]2[C@H:69]([C:73]([OH:75])=[O:74])[CH2:70][CH2:71][CH2:72][C@@H:65]2[CH2:64][CH:63]=[CH:62][CH2:61]1)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1
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Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 22149038(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl esterHCID 69659568(4S,7S,11aS)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acidHCID 86590807(4S,7S,11aR)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic Acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

Produkt 1

HCID 69659744
(4S,7S,11aR)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Preparation of (4S,7S,11aR)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide (45) A catalytic amount of Pd(Ph3P)4 (35 mg, 0.03 mmol) is added to a solution of (2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl ester (69 mg, 0.3 mmol) and N,N-dimethylbarbituric acid (156 mg, 1.0 mmol) in 2 mL CH2Cl2 at room temperature. The solution is stirred at rt for 15 minutes and (4S,7S,11aS)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid, 44, (40 mg, 0.12 mmol) is added as a solution in 1 mL CH2Cl2, followed by 1-hydroxybenzotriazole (41 mg, 0.3 mmol) and 1-(3-dimethyl-aminopropyl)-3-ethyl-carbodiimide hydrochloride (58 mg, 0.3 mmol). The solution is stirred for 4 hours, diluted with EtOAc, washed with saturated NaHCO3 and brine, dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography over silica gel afforded 32 mg of the desired product. 1H NMR (CDCl3) δ 7.88 (m, 2H), 7.72 (m, 1H), 7.51 (m, 3H), 5.75–5.25 (series of m, 4H), 5.02 (d, J=5.8 Hz, 1H), 4.66 (m, 2H), 3.98 (dq, J=9.3, 7.0 Hz, 1H), 3.73 (dq, J=9.3, 7.0 Hz, 1H), 3.24 (m, 1H), 2.96–1.45 (series of m, 11H), 1.37 (t, J=7.0 Hz, 3H); MS 470 (M+H)+.

Aufarbeitung

  1. stirringThe solution is stirred for 4 hours
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-da8aca8e73c746f4bc865eb98655fb53
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07138395B2

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