Water → HCID 66976211, compound

HRID 1022756Notes

Reaction equation

HRID 1022756 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([NH:10][CH2:11][C@H:12]2[C@H:18]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([F:26])[CH:20]=3)[O:17][CH2:16][CH2:15][N:14]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13]2)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:36][S:37](Cl)(=[O:39])=[O:38].O>CN(C=O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C@@H:18]2[O:17][CH2:16][CH2:15][N:14]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13][C@H:12]2[CH2:11][NH:10][C:8]([C:3]2[C:2]([NH:1][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:7][CH:6]=[CH:5][N:4]=2)=[O:9])=[CH:20][C:21]=1[F:26]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 66976757HCID 66976757, compound

Product 1

HCID 66976211HCID 66976211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (6R,7R)-6-({[(3-aminopyridin-2-yl)carbonyl]amino}methyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate (110 mg) in DMF (3 ml) was added 60% sodium hydride at 0° C., and the mixture was stirred for 30 min. Methanesulfonyl chloride (53 μL) was added, and the mixture was warmed to room temperature, and stirred overnight. The reaction mixture was poured into water, and the mixture was partitioned twice with ethyl acetate. The organic layers were combined, and the mixture was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (44.4 mg).

Workup

  1. stirringstirred overnight
  2. customthe mixture was partitioned twice with ethyl acetate
  3. washthe mixture was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4219f4dbcc024af89c602a365eff61f8
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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