Methanesulfonamide → HCID 66975511, compound

HRID 1022680Notes

Reaction equation

HRID 1022680 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C@@H:13]([CH2:15][O:16][C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19](O)=[O:20])[C@H:12]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][S:35]([NH2:38])(=[O:37])=[O:36].Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Cl:33][C:28]1[CH:27]=[C:26]([C@@H:12]2[O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:14][C@H:13]2[CH2:15][O:16][C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19](=[O:20])[NH:38][S:35]([CH3:34])(=[O:37])=[O:36])[CH:31]=[CH:30][C:29]=1[Cl:32]

Participants

7

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66976199HCID 66976199, compound

Product 1

HCID 66975511HCID 66975511, compoundYield 34.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-{[(6S,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]methoxy}benzoic acid (100 mg) in DMF (1 ml) were added methanesulfonamide (38.3 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (62.5 mg) and N,N-dimethyl-4-aminopyridine (49.2 mg) at room temperature, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (40 mg).

Workup

  1. washThe diluted solution was washed with distilled water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9162849b6fa94a548fb670125e2a65ab
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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