Dichloromethane → HCID 59006363, compound

HRID 1867605Notes

Reaction equation

HRID 1867605 reaction equation
[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O.[NH2:17][C:18]([C:20]1[NH:21][C:22](=[O:38])[N:23]([CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)[CH:24]=1)=O.ClCCl.C(=O)(O)[O-].[Na+]>ClC(Cl)C>[C:18]([C:20]1[NH:21][C:22](=[O:38])[N:23]([CH:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:29][CH2:30]2)[CH:24]=1)#[N:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 59006367Tert-butyl 4-(4-carbamoyl-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 59006363HCID 59006363, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

(Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt (179.7 mg, 0.754 mmol) was added to a solution of tert-butyl 4-[4-(aminocarbonyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]piperidine-1-carboxylate (78 mg, 0.251 mmol) in dichloroethane (5 mL) and was heated to 50° C. After 1 h, the reaction was worked up with dichloromethane and saturated sodium bicarbonate. The organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→5% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (40 mg). MS 237.04 (M+1-tert butyl)

Workup

  1. washThe organic extracts were washed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (100% dichloromethane→5% methanol {1% ammonium hydroxide}/dichloromethane)

Sources & evidence

ORD record
ord-05f908f0430b4cd795b481588415ca9f
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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