HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

2-Dimethylaminopyridine → N-butanesulfonyl-(t-butoxycarbonyl)valineamide

HRID 1941342
Notes
Print preview

Reaction equation

HRID 1941342 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:25](F)=[O:26])[CH:22]([CH3:24])[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:25](=[O:26])[C@H:21]([CH:22]([CH3:23])[CH3:24])[NH:20][C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 218852-DimethylaminopyridineHCID 10751345t-Butoxycarbonylvaline fluorideHCID 86751785N-butanesulfonyl-N-trimethylsilylamide

Product 1

HCID 22880656N-butanesulfonyl-(t-butoxycarbonyl)valineamide

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of N-butanesulfonyl-N-trimethylsilylamide (prepared according to the procedure described in Example 8) (1.72 g, 8.28 mmol), t-butoxycarbonylvaline fluoride (1.01 g, 4.6 mmol), and dimethylaminopyridine (220 mg, 1.84 mmol) in tetrahydrofuran (25 ml) is stirred at room temperature for 1 hour. 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 (3:1) to give N-butanesulfonyl-(t-butoxycarbonyl)valineamide.

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 (3:1)

Sources & evidence

ORD record
ord-502a98148e104dd6a1c7a1947e0e17df
Source dataset
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05703106

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes