Ammonium Chloride → tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-[(2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl)methyl]-1,4-oxazepane-4-carboxylate

HRID 1022800Notes

Reaction equation

C[O-].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([CH:12]2[CH:18]([CH2:19][NH:20][C:21](=[O:33])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([O:31]C)=O)[O:17][CH2:16][CH2:15][N:14]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11].[Cl-].[NH4+]>CO>[Cl:4][C:5]1[CH:6]=[C:7]([CH:12]2[CH:18]([CH2:19][N:20]3[C:29](=[O:31])[C:24]4[C:23](=[CH:28][CH:27]=[CH:26][CH:25]=4)[NH:22][C:21]3=[O:33])[O:17][CH2:16][CH2:15][N:14]([C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])[CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A 28% solution (0.2 ml) of sodium methoxide in methanol was added dropwise to a solution of tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-[({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)methyl]-1,4-oxazepane-4-carboxylate (190 mg) in methanol (5 mL), and the mixture was stirred at 80° C. for 1 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (135 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-ff36ea3383e141479fe23a0f49b1a89f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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