Dimethylformamide → HCID 69229591, compound

HRID 656311Notes

Reaction equation

HRID 656311 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].CN[NH:21][S:22](Cl)(=[O:24])=[O:23].[CH3:26]N(C)C=O>>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][S:22]([NH:21][CH3:26])(=[O:24])=[O:23])=[CH:14][CH:13]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 20229151HCID 20229151, compound

Product 1

HCID 69229591HCID 69229591, compoundYield 79%

Procedure

Sodium hydride (18 mg) was suspended in dimethylformamide, and to the suspension was added a solution of N-t-butyloxycarbonyl-p-aminobenzylamine (150 mg) and methylaminosulfamoylchloride (97 mg) in dimethylformamide while the temperature was controlled to 0° C., followed by stirring at room temperature for 3 hours. The reaction solution was evaporated under reduced pressure, and the residue was diluted with ethyl acetate (70 ml), washed with saturated aqueous sodium bicarbonate solution, water and saturated saline, and then evaporated under reduced pressrure. The obtained residue was purified by column-chromatography (hexane/ethyl acetate=5/1) to yield the compound 35-1a (170 mg, 79%).

Workup

  1. customwas controlled to 0° C.
  2. customThe reaction solution was evaporated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate (70 ml)
  4. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated saline
  5. customevaporated under reduced pressrure
  6. customThe obtained residue was purified by column-chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-9f396d4abc0244378d46c00d7be524a2
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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