Dimethylformamide → HCID 11237517, compound

HRID 1375619Notes

Reaction equation

HRID 1375619 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@H:16]([NH:19][S:20]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([Cl:33])[CH:29]=4)[CH:24]=3)(=[O:22])=[O:21])[C:15]2=[O:34])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:35](=[O:38])([O-])[O-:36].[K+].[K+].BrCC(O[C:46](C)([CH3:48])[CH3:47])=O.[CH3:50]N(C=O)C>>[Cl:33][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([S:20]([N:19]([CH2:50][C:35]([OH:36])=[O:38])[C@H:16]1[CH2:17][CH2:18][N:14]([CH:11]3[CH2:12][CH2:13][N:8]([CH:46]([CH3:48])[CH3:47])[CH2:9][CH2:10]3)[C:15]1=[O:34])(=[O:21])=[O:22])[CH:32]=[CH:31]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 11752537HCID 11752537, compound

Product 1

HCID 11237517HCID 11237517, compound

Procedure

To a mixture of 4-[3-(6-chloro-naphthalene-2-sulfonylamino)-2-oxo-pyrrolidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (example 19, 57 mg, 0.11 mmol) in DMF (3.0 mL) at 0° C. were added potassium carbonate (50 mg) and tert-butyl bromoacetate (0.1 mL). After stirring for 2 hr, the mixture was filtered. The filtrate was purified by HPLC (60% to 100% acetonitril/water gradient) and the desired product was obtained as a solid. LC-MS found: (M+1)+=622.54.

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was purified by HPLC (60% to 100% acetonitril/water gradient)

Sources & evidence

ORD record
ord-1275750524ca4120ae4999be02e8cc02
Source dataset
uspto-grants-2007_01
Patent number
US07169795B2

Reaction notes

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