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Water → 4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid

HRID 2249964
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Reaktionsgleichung

Reaktionsgleichung von HRID 2249964
[C:1]([O:5][C:6](=[O:33])[CH2:7][C@@H:8]([CH2:24][CH:25]1[CH2:32][CH2:31][C:28]2([CH2:30][CH2:29]2)[CH2:27][CH2:26]1)[C:9]([N:11]1[C@@H:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][O:13][C:12]1=[O:23])=[O:10])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.O>O1CCOCC1>[C:1]([O:5][C:6](=[O:33])[CH2:7][C@@H:8]([CH2:24][CH:25]1[CH2:26][CH2:27][C:28]2([CH2:29][CH2:30]2)[CH2:31][CH2:32]1)[C:9]([N:11]1[C@@H:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][O:13][C:12]1=[O:23])=[O:10])([CH3:4])([CH3:2])[CH3:3].[CH2:16]([C@H:15]1[CH2:14][O:13][C:12](=[O:23])[N:11]1[C:9](=[O:10])[C@H:8]([CH2:24][CH:25]1[CH2:32][CH2:31][C:28]2([CH2:29][CH2:30]2)[CH2:27][CH2:26]1)[CH2:7][C:6]([OH:33])=[O:5])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 684829284-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid tert-butyl ester

Produkt 2

HCID 684825934-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acidAusbeute 278,1 %
HCID 684829284-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid tert-butyl ester was prepared according to the procedures described in Example 26. A modified procedure was used for the t-Butyl ester deprotection from Trzeciak, A. et al. Synthesis 1996, 1443. 4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid tert-butyl ester (40 mg, 0.09 mmol, 1.0 eq.) was dissolved in dry dioxane (5 mL) under nitrogen followed by addition of Et3N (200 μL, 1.43 mmol, 16 eq.) and TMS-OTf (200 μL, 1.11 mmol, 12.3 eq.) via syringe. The reaction mixture stirred at room temperature overnight and then heated to 65° C. for 1.5 hours. Upon completion, 2 mL of water was added and volatiles were evaporated. The product was diluted with ethyl ether and extracted with water, and brine. The organic layer was dried over MgSO4, filtered and evaporated to provide 4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid (50 mg, quantitative) as white solid and used directly in the next step. HPLC-MS calcd. for C23H29NO5 (M+Na+) 422.2. found 422.1. 4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid was converted to the title compound according to the procedures described in example 21.

Aufarbeitung

  1. customet al. Synthesis 1996, 1443
  2. temperatureheated to 65° C. for 1.5 hours
  3. customvolatiles were evaporated
  4. additionThe product was diluted with ethyl ether
  5. extractionextracted with water, and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3d06813cc427483e9267bfe06f0fcb41
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07314872B2

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