Triethylamine → tert-butyl (6R,7S)-7-(3,4-dichlorophenyl)-6-[(methylsulfamoyl)amino]-1,4-oxazepane-4-carboxylate

HRID 1022729Notes

Reaction equation

[NH2:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[O:7][CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1.[CH3:24][NH:25][S:26](=O)(=[O:35])[O:27]C1C=CC=CC=1O.C(N(CC)CC)C>C(#N)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Cl:16][C:11]1[CH:10]=[C:9]([C@@H:8]2[O:7][CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3][C@H:2]2[NH:1][S:26](=[O:35])(=[O:27])[NH:25][CH3:24])[CH:14]=[CH:13][C:12]=1[Cl:15]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (100 mg) in acetonitrile (3 mL) were added 2-hydroxyphenyl methylsulfamate (86 mg), triethylamine (56 mg) and N,N-dimethyl-4-aminopyridine (3.3 mg) at room temperature, and the mixture was stirred at 80° C. overnight. 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 (81 mg).

Workup

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

Sources & evidence

ORD record: ord-bad1ae98df514fdfa244905d77be787c
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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