Ammonium Chloride → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(methylsulfonyl)carbamoyl]-1,4-oxazepane-4-carboxylate

HRID 1022720Notes

Reaction equation

HRID 1022720 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C@@H:13]([C:15](O)=[O:16])[C@H:12]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][S:27]([NH2:30])(=[O:29])=[O:28].CC1C=CC=C([N+]([O-])=O)C=1C(OC(=O)C1C([N+]([O-])=O)=CC=CC=1C)=O.[Cl-].[NH4+]>C(#N)C.CN(C1C=CN=CC=1)C>[Cl:25][C:20]1[CH:19]=[C:18]([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[C:15](=[O:16])[NH:30][S:27]([CH3:26])(=[O:29])=[O:28])[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 72879MethanesulfonamideHCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 66975341(6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid

Product 1

HCID 66975840tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(methylsulfonyl)carbamoyl]-1,4-oxazepane-4-carboxylateYield 45.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of (6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid (590 mg) in acetonitrile (15.1 mL) were added N,N-dimethyl-4-aminopyridine (203 mg), methanesulfonamide (158 mg) and 2-methyl-6-nitrobenzoic anhydride (625 mg) at room temperature, and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract 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 (323 mg).

Workup

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

Sources & evidence

ORD record
ord-d535f10a6c344f2aa24ff8c90fbeb8c8
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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