Dimethylsulphamoyl chloride → HCID 69329303, compound

HRID 1351879Notes

Reaction equation

HRID 1351879 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([N:11]([CH2:19][C@H:20]([OH:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][C:4]=2[CH:3]=1.[CH3:32][N:33]([CH3:38])[S:34](Cl)(=[O:36])=[O:35].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[CH3:32][N:33]([CH3:38])[S:34]([NH:1][C:2]1[CH:31]=[CH:30][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([N:11]([CH2:19][C@H:20]([OH:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][C:4]=2[CH:3]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 83372Dimethylsulphamoyl chlorideHCID 516892Sodium BicarbonateHCID 57152468HCID 57152468, compound

Product 1

HCID 69329303HCID 69329303, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under nitrogen, a solution of (2S)-1-[N-(3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-benzylamino]-3-phenoxy-2-propanol (150 mg), dimethylaminosulfonyl chloride (43 μl) and pyridine (31 μl) in toluent (5 ml) was stirred at 80° C. for 24 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give (2S)-1-[N-(3-dimethylaminosulfonylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-benzylamino]-3-phenoxy-2-propanol (156 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-eb216824210d4dafb8630d899a79f7e0
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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