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

HRID 1783878Notes

Reaction equation

HRID 1783878 reaction equation
[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

Participants

7

Reactant 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

Product 2

HCID 684825934-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acidYield 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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a19edd48a1ea4ba5bb67556f5e63ca3f
Source dataset
uspto-grants-2009_03
Patent number
US07501408B2

Reaction notes

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