Methyl iodide → HCID 18727283, compound

HRID 842989Notes

Reaction equation

HRID 842989 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[Cl:9][C:10]1[CH:38]=[CH:37][C:13]([C:14]([CH:16]2[CH2:21][CH2:20][N:19]([S:22]([NH:25][C@H:26]([CH:34]([CH3:36])[CH3:35])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])(=[O:24])=[O:23])[CH2:18][CH2:17]2)=[O:15])=[CH:12][CH:11]=1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][N:25]([S:22]([N:19]1[CH2:20][CH2:21][CH:16]([C:14](=[O:15])[C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:38][CH:37]=2)[CH2:17][CH2:18]1)(=[O:23])=[O:24])[C@H:26]([CH:34]([CH3:35])[CH3:36])[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18727281HCID 18727281, compound

Product 1

HCID 18727283HCID 18727283, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Anhydrous potassium carbonate (152 mg, 1.1 mmol) and iodomethane (0.034 ml, 0.5 mmol) were added to a solution of tert-butyl 2-(R)-{[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]amino}-3-methylbutyrate (100 mg, 0.22 mmol) in DMF (1.5 ml) at RT. After 3 h, the reaction mixture was diluted with ethyl acetate (30 ml) and then washed with 0.1M HCl and brine, and dried over MgSO4. The solvent was removed in vacuo and the residue was chromatographed (PTLC, SiO2, 25% ethyl acetate/hexane) to give tert-butyl 2-(R)-{methyl-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]amino}-3-methylbutyrate as a colorless oil (63%).

Workup

  1. washwashed with 0.1M HCl and brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customthe residue was chromatographed (PTLC, SiO2, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-df0a694419a943989ceb2fd6b5594fd0
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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