2-Dimethylaminopyridine → HCID 70092293, compound

HRID 1941337Notes

Reaction equation

HRID 1941337 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:32](F)=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[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:32](=[O:33])[C@H:21]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH:20][C:18]([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:19])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 218852-DimethylaminopyridineHCID 10979687t-Butoxycarbonyltryptophan fluorideHCID 86751785N-butanesulfonyl-N-trimethylsilylamide

Product 1

HCID 70092293HCID 70092293, compound

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-butanesulfonyl-N-trimethylsilylamide (0.75 g, 3.6 mmol), t-butoxycarbonyltryptophan fluoride (0.92 g, 3.01 mmol), and dimethylaminopyridine (37 mg, 0.3 mmol) in tetrahydrofuran (10 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 (1:1) and trace of acetic acid to give N-butanesulfonyl-(t-butoxycarbonyl)tryptophanamide.

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 (1:1) and trace of acetic acid

Sources & evidence

ORD record
ord-21ac40b472934c85b3b1f9128507e183
Source dataset
uspto-grants-1997_12
Patent number
US05703106

Reaction notes

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