Acetic Acid → HCID 58313168, compound

HRID 535142Notes

Reaction equation

HRID 535142 reaction equation
CC([Si](C)(C)[O:6][CH:7]1[CH2:10][C:9]2([CH2:14][CH:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:11]2)[CH2:8]1)(C)C.C(O)(=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][CH:7]1[CH2:8][C:9]2([CH2:14][CH:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[CH2:11]2)[CH2:10]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 58313154HCID 58313154, compound

Product 1

HCID 58313168HCID 58313168, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 7-ethyl 6-(phenylmethyl) 2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-6-azaspiro[3.4]octane-6,7-dicarboxylate (151) (1.87 g, 4.2 mmol) in THF (20 mL) was added glacial acetic acid (0.48 mL), followed by TBAF (8.5 mL, 1M solution in THF) and the reaction heated to 45° C. for 18 h. The reaction was concentrated in vacuo and partitioned between EtOAc and water. The organic layer was washed with saturated NaHCO3 followed by brine, and then dried over MgSO4 and concentrated in vacuo to afford the title compound as a clear oil in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.17-7.48 (m, 5H) 4.83-5.15 (m, 3H) 3.88-4.34 (m, 4H) 3.35-3.47 (m, 2 H) 2.02-2.39 (m, 3H) 1.65-1.96 (m, 3H) 1.00-1.22 (m, 3H). LC-MS ESI (M+H)+=334.17.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70907506917045abbff098699b13143e
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

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