Triethylamine → HCID 57295678, compound

HRID 1078723Notes

Reaction equation

HRID 1078723 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si](C(C)(C)C)(C)C)[CH2:10][C@H:9]1[C:21](=[O:30])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].C(N(CC)CC)C.[CH3:58][S:59](Cl)(=[O:61])=[O:60]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:59]([CH3:58])(=[O:61])=[O:60])[CH2:10][C@H:9]1[C:21](=[O:30])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium Chloride2×HCID 31297Methanesulfonyl chlorideHCID 2724141Tetrabutylammonium FluorideHCID 22865012HCID 22865012, compound

Product 1

HCID 57295678HCID 57295678, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,4R)-N-tert-butoxycarbonyl-2-(2-tert-butoxycarbonyl-1-oxoethyl)-4-tert-butyldimethylsiloxypyrrolidine (3.39 g, 7.64 mmol) in tetrahydrofuran (35 ml) was added a 1M tetrabutylammonium fluoride--tetrahydrofuran solution (8.41 ml, 8.41 mmol). This solution was stirred at room temperature for 8 h. Saturated aqueous ammonium chloride was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. The residue was dissolved in methylene chloride (50 ml), and triethylamine (3.22 ml, 22.9 mmol) and methanesulfonyl chloride (1.18 ml, 15.3 mmol) were successively dropwise added thereto at 0° C. The mixture was stirred at the same temperature for 2 h. Then, saturated aqueous ammonium chloride was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (heptane-ethyl acetate=1:1) to obtain the title compound (2.33 g, yield: 74.8%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride (50 ml)
  6. customat 0° C
  7. stirringThe mixture was stirred at the same temperature for 2 h
  8. extractionThe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed in vacuo
  12. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c031e3f145bf47db85cedf35f9894ab1
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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