Dimethylformamide → HCID 86682291, compound

HRID 529727Notes

Reaction equation

HRID 529727 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Br:26])[CH:19]=2)[C:14]([OH:17])([CH3:16])[CH3:15])(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].C[N:32]([CH:34]=[O:35])C>CCOC(C)=O.CCCCCC.O>[Br:26][C:20]1[CH:19]=[C:18]([C@@H:13]2[C:14]([CH3:15])([CH3:16])[O:17][C:34](=[O:35])[NH:32][CH2:12]2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86682293HCID 86682293, compound

Product 1

HCID 86682291HCID 86682291, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-2-(3-bromo-4-methoxyphenyl)-3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (58 mg, 0.13 mmol) in 2 mL DMF was added NaN3 (34 mg, 0.52 mmol). The resulting reaction mixture was heated at 60° C. overnight and was then diluted with 10 mL EtOAc/hexane (1:1) and 10 mL water. The layers were separated. The organics were dried over sodium sulfate, filtered and concentrated. Crude product was purified on Combiflash prepacked silica gel column, eluted with hexane to 40% EtOAc in hexane to give 38 mg desired product. 1H NMR (500 MHz, CDCl3): δ 7.49 (d, J=1.9 Hz, 1H), 7.22 (dd, J=2.1, 8.5 Hz, 1H), 6.91 (d, J=8.4 Hz, 1H), 3.93 (s, 3H), 3.9 (m, 1H), 3.71 (m, 1H), 2.82 (m, 1H), 1.28 (s, 3H), 1.17 (s, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customThe layers were separated
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customCrude product was purified on Combiflash prepacked silica gel column
  7. washeluted with hexane to 40% EtOAc in hexane

Sources & evidence

ORD record
ord-363fe10d35884083994ab7fbb63d37ca
Source dataset
uspto-grants-2016_05
Patent number
US09346825B2

Reaction notes

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