2,4,6-Triisopropylbenzenesulfonyl azide → HCID 53941532, compound

HRID 974879Notes

Reaction equation

HRID 974879 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:26][CH:27]=[CH2:28])[CH2:10][C:11]([N:13]2[C@@H:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:16][O:15][C:14]2=[O:25])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=C([C@@H](C=CC)CC(O)=O)C=CC=1Cl.C([C@H]1COC(=O)N1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].CC(C1C=C(C(C)C)C(S([N:83]=[N+:84]=[N-:85])(=O)=O)=C(C(C)C)C=1)C>C1COCC1.O.CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:26][CH:27]=[CH2:28])[C@H:10]([N:83]=[N+:84]=[N-:85])[C:11]([N:13]2[C@@H:17]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:16][O:15][C:14]2=[O:25])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

9

Reactant 5

HCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 54423383HCID 54423383, compoundHCID 54464961HCID 54464961, compound

Product 1

HCID 53941532HCID 53941532, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 3-(3(S)-(3,4-dichlorophenyl)-1-oxo-5-hexenyl)-4(S)-benzyl-2-oxazolidinone (190 mg, 0.45 mmol; prepared from 3-(R)-(3,4-dichlorophenyl)-hex-4-enoic acid (from Step B above) and 4(S)-benzyl-2-oxazolidinone according to the procedure of Evans, D. A.; et. al. J. Am. Chem. Soc. 1990, 112, 4011-4030) in THF (2.5 mL) was added to a solution of KHMDS (1.0 mL of 0.5M in PhCH3, 0.50 mmol), and THF (1.5 mL) at -78° C. The reaction was maintained at -78° C. for 30 min whereupon a solution of trisyl azide (177 mg, 0.57 mmol) and THF (1.5 mL) was added. The mixture was stirred for 2 min and HOAc (0.13 mL, 4.6 mmoL) was added. The reaction mixture was stirred 1 h in a 30° C. water bath, whereupon it was diluted with H2O (50 mL) and extracted with CH2Cl2 (3×30 mL). The combined organic extracts were washed with sat. aq. NaHCO3, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel 60, 15-25% EtOAc/hexanes) to afford the title compound (169 mg, 81%) as a colorless oil.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred 1 h in a 30° C. water bath
  3. extractionextracted with CH2Cl2 (3×30 mL)
  4. washThe combined organic extracts were washed with sat. aq. NaHCO3, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel 60, 15-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-44978b54f32b47fcaa5823b3535efdba
Source dataset
uspto-grants-1997_03
Patent number
US05607936

Reaction notes

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