2-Dimethylaminopyridine → HCID 22880655, compound

HRID 1941340Notes

Reaction equation

HRID 1941340 reaction equation
[CH2:1]([S:5]([N-:8][Si](C)(C)C)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[C:13]([O:17][C:18]([NH:20][C@H:21]([C:26](F)=[O:27])[C@H:22]([CH2:24][CH3:25])[CH3:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].CN(C1C=CC=CN=1)C>O1CCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:1]([S:5]([NH:8][C:26](=[O:27])[C@H:21]([C@H:22]([CH2:24][CH3:25])[CH3:23])[NH:20][C:18]([O:17][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:19])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 218852-DimethylaminopyridineHCID 14824271HCID 14824271, compoundHCID 86751785N-butanesulfonyl-N-trimethylsilylamide

Product 1

HCID 22880655HCID 22880655, compound

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-butanesulfonyl-N-trimethylsilylamide (prepared according to the procedure described in Example 8) (0.64 g, 3.06 mmol), t-butoxycarbonylisoleucine fluoride (0.475 g, 2.04 mmol), and dimethylaminopyridine (110 mg, 0.9 mmol) in tetrahydrofuran (7 ml) is stirred at room temperature for 2 hours. The mixture is diluted with 10% citric acid and extracted with ethyl acetate. The organic layer is washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The crude material is chromatographed on silica gel with ethyl acetate/hexane (4:1) to give N-butanesulfonyl-(t-butoxycarbonyl)isoleucineamide.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material is chromatographed on silica gel with ethyl acetate/hexane (4:1)

Sources & evidence

ORD record
ord-288cff24715443eaba2207a2ebfd9030
Source dataset
uspto-grants-1997_12
Patent number
US05703106

Reaction notes

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