Diisopropylethylamine → HCID 86746959, compound

HRID 1655087Notes

Reaction equation

HRID 1655087 reaction equation
[O-]S(C(F)(F)F)(=O)=O.C([B+]CCCC)CCC.[CH:18]([CH:21]1[CH2:26][CH2:25][O:24][C:23](=[O:27])[N:22]1[C:28](=[O:39])[CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])([CH3:20])[CH3:19].C(N(C(C)C)CC)(C)C.[CH2:49]([N:55]1[C:59]([CH:60]=[O:61])=[CH:58][N:57]=[CH:56]1)[CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]>ClCCl>[CH2:49]([N:55]1[C:59]([C@@H:60]([OH:61])[C@@H:29]([C:28]([N:22]2[C@H:21]([CH:18]([CH3:20])[CH3:19])[CH2:26][CH2:25][O:24][C:23]2=[O:27])=[O:39])[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:58][N:57]=[CH:56]1)[CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 20077574HCID 20077574, compoundHCID 86748650HCID 86748650, compoundHCID 178418657HCID 178418657, compound

Product 1

HCID 86746959HCID 86746959, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
5 °C

Procedure

A 1M solution of dibutylboron triflate in dichloromethane (1.56 ml) was added to a solution of the product of step (iv) (422 mg, 1.42 mmol) in dry dichloromethane (9 ml) at 5° C. under argon, followed by diisopropylethylamine (0.295 ml, 1.7 mmol). The reaction mixture was stirred at 5° C. for 30 minutes and then cooled to -78° C. A solution of the product of step (iii) (280 mg, 1.56 mmol) in dichloromethane (2 ml) was added dropwise. The mixture was stirred at -78° C. for 30 minutes before being allowed to warm to room temperature. The reaction was quenched by the addition of pH7.2 phosphate buffer solution (1.36 ml) followed by hydrogen peroxide (0.4 ml, 30% w/v aqueous solution). The mixture was stirred for 30 minutes and then poured into water and extracted three times with dichloromethane. The combined extracts were dried (MgSO4), filtered, and evaporated. The residue was purified by column chromatography, eluting with ethyl acetate, to give methyl (7S,4Z)-7-[(S)-(1-hexylimidazol-5-yl)hydroxymethyl]-8-[(S)-4-isopropyl-2-oxo-1,3-oxazinan-3-yl]-8-oxo-oct-4-enoate (450 mg, 66% yield) as an oil;

Workup

  1. temperaturecooled to -78° C
  2. stirringThe mixture was stirred at -78° C. for 30 minutes
  3. temperatureto warm to room temperature
  4. customThe reaction was quenched by the addition of pH7.2 phosphate buffer solution (1.36 ml)
  5. stirringThe mixture was stirred for 30 minutes
  6. additionpoured into water
  7. extractionextracted three times with dichloromethane
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography
  12. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0727786e481b4f148b71e7bb7679cec1
Source dataset
uspto-grants-1995_04
Patent number
US05410064

Reaction notes

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