Acetic Acid → HCID 86761240, compound

HRID 2265260Notes

Reaction equation

HRID 2265260 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:31])[CH2:15][CH:16]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(C1C=C(C(C)C)C=C(C(C)C)C=1S([N:60]=[N+:61]=[N-:62])(=O)=O)(C)C.CC(O)=O>C1COCC1>[N:60]([C@@H:15]([CH:16]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:14]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:31])=[N+:61]=[N-:62]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 68771144HCID 68771144, compound

Product 1

HCID 86761240HCID 86761240, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-(S)-benzyl-3-[3,3-bis-(4-chloro-phenyl)-propionyl]-oxazolidin-2-one (2.0 g, 4.4 mmol) in THF (25 mL) was cooled to −78° C. and added via cannula to a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 9.7 mL, 4.8 mmol) in THF (15 mL) at −78° C. After 30 min at −78° C., a solution of 2,4,6-triisopropylbenzenesulfonyl azide (1.77 g, 5.7 mmol) in THF (15 mL) was cooled to −78° C. and added via cannula. After 1 min, the reaction was quenched by addition of AcOH (1.2 mL, 21 mmol). The cooling bath was removed, and the mixture was allowed to warm to rt and stir overnight. The reaction mixture was diluted with water and extracted with DCM (3×). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (EtOAc/hexanes) to provide 1.58 g (72%) of the desired azide as a white foam. 1H NMR (400 MHz, CDCl3): 7.38-7.15 (m, 13H), 5.94 (d, J=11.0, 1H), 4.50 (d, J=11.0, 1H), 4.34-4.25 (m, 1H), 4.08 (dd, J=9.2, 2.4, 1H), 3.76 (dd, J=8.8, 8.1, 1H), 3.22 (dd, J=13.5, 3.3, 1H), 2.77 (dd, J=13.5, 9.5, 1H).

Workup

  1. additionadded via cannula
  2. waitAfter 1 min
  3. customThe cooling bath was removed
  4. additionThe reaction mixture was diluted with water
  5. extractionextracted with DCM (3×)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-f4ed999f29d34625b5e303f321db4df7
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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