Diisopropylethylamine → HCID 69597691, compound

HRID 724684Notes

Reaction equation

HRID 724684 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[S:16](=[O:18])(=[O:17])[NH:15][C:14](=[O:19])[CH2:13]2)=[C:8]([Br:20])[CH:7]=1)(=[O:3])[CH3:2].[CH:21](N(CC)C(C)C)(C)C.[CH3:30][Si:31]([CH3:38])([CH3:37])[CH2:32][CH2:33][O:34]CCl>C(#N)C>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[S:16](=[O:18])(=[O:17])[N:15]([O:34][CH2:33][CH2:32][Si:31]([CH3:38])([CH3:37])[CH3:30])[C:14](=[O:19])[CH:13]2[CH3:21])=[C:8]([Br:20])[CH:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 58746801HCID 58746801, compound

Product 1

HCID 69597691HCID 69597691, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

3-Bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzyl acetate (175 mg, 0.483 mmol) was dissolved in acetonitrile (1.0 mL) and N,N-diisopropylethylamine (126 μL, 0.725 mmol) was added followed by [β-(trimethylsilyl)ethoxy]methyl chloride (103 μL, 0.580 mmol), and the reaction was heated at 50° C. for 1 h. Reaction solution was cooled to room temperature and transferred to separatory funnel, partitioned between 0.1 N HCl solution and ethyl acetate, aqueous phase was washed with ethyl acetate. The combined organic phase was washed with saturated sodium chloride, dried over sodium sulfate and concentrated to give a yellow oil. This material was chromatographed (12 g column, 0–20% ethyl acetate/hexanes) to give the product as an oil (193 mg, 81%). 1H NMR (400 MHz, CDCl3): δ 7.70 (s, 1H), 7.37 (m, 2H), 5.53 (dd, J=8.0, 6.5 Hz, 1H), 5.06 (m, 4H), 3.65 (m, 2H), 3.49 (dd, J=17.4, 8.0 Hz, 1H), 3.23 (dd, J=17.4, 6.5 Hz, 1H), 2.13 (s, 3H), 0.95 (m, 2H), 0.0 (s, 9H).

Workup

  1. customReaction solution
  2. temperaturewas cooled to room temperature
  3. customtransferred to separatory funnel
  4. custompartitioned between 0.1 N HCl solution and ethyl acetate, aqueous phase
  5. washwas washed with ethyl acetate
  6. washThe combined organic phase was washed with saturated sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a yellow oil
  10. customThis material was chromatographed (12 g column, 0–20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6c2dfe4761214a1780487f56b786de7e
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

Loading…