Phenylmethanesulfonyl chloride → HCID 86592601, compound

HRID 413871Notes

Reaction equation

HRID 413871 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[C:12](=[O:13])[CH:11]([CH3:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[C:8]2[C:19]([NH2:23])=[CH:20][CH:21]=[CH:22][C:7]1=2)=[O:5])[CH3:3].[CH2:24]([S:31](Cl)(=[O:33])=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:24]([S:31]([NH:1][C@H:2]([C:4]([N:6]1[C:12](=[O:13])[CH:11]([CH3:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[C:8]2[C:19]([NH2:23])=[CH:20][CH:21]=[CH:22][C:7]1=2)=[O:5])[CH3:3])(=[O:33])=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 697363355-(L-alaninyl)-amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one

Product 1

HCID 86592601HCID 86592601, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-(L-alaninyl)-amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one (Example 7B) (0.2050 g, 0.66 mmol) in DMF (5 ml) was added benzylsulfonyl chloride (Aldrich) (0.0632 g, 0.33 mmol), stirred at RT for 3.5 days. The reaction mixture was evaporated to dryness. Water was added, extracted with CH2Cl2, washed with brine, dried over MgSO4. Evaporation and flash chromatography (silica, 5% MeOH /CH2Cl2), gave a residue, which was washed with Et2O /hexane (1:2, v/v) to give the title compound (0.0531 g, 35%) as a light yellow solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionWater was added
  3. extractionextracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customEvaporation and flash chromatography (silica, 5% MeOH /CH2Cl2)
  7. customgave a residue, which
  8. washwas washed with Et2O /hexane (1:2

Sources & evidence

ORD record
ord-b3bfb28d08d748e4b4fd6133164e2c8f
Source dataset
uspto-grants-2003_05
Patent number
US06569851B1

Reaction notes

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