Sodium Carbonate → HCID 18983320, compound

HRID 1729504Notes

Reaction equation

HRID 1729504 reaction equation
Br[C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][N:12]3[C:16]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH:22]4[CH2:24][CH2:23]4)[N:14]=[C:13]3[CH2:25][CH3:26])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.[Pd]>[CH:22]1([C:15]2[N:14]=[C:13]([CH2:25][CH3:26])[N:12]([CH2:11][C:8]3[CH:9]=[CH:10][C:5]4[O:4][C:3]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[NH:33][S:34]([C:37]([F:40])([F:38])[F:39])(=[O:36])=[O:35])=[CH:2][C:6]=4[CH:7]=3)[C:16]=2[C:17]([NH:19][CH2:20][CH3:21])=[O:18])[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 10032066HCID 10032066, compound

Product 1

HCID 18983320HCID 18983320, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 8 (0.25 g) in ethyl acetate (15 ml) was stirred under a hydrogen atmosphere over 10% palladium on carbon (0.3 g; 50% aqueous paste) at room temperature for 3 h. Solid sodium carbonate (70 mg) was added and the reaction continued for a further 4 h. The mixture was filtered and the filtrate evaporated. The residue was purified by column chromatography eluting with System F (20:1) increasing to (5:1) to give the title compound as a white powder (0.11 g), m.p. 165°-172°.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customThe residue was purified by column chromatography
  4. washeluting with System F (20:1)
  5. temperatureincreasing to (5:1)

Sources & evidence

ORD record
ord-6fe64cf026d94495beae045794bd14aa
Source dataset
uspto-grants-1994_07
Patent number
US05332831

Reaction notes

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