Methylhydrazine → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[4-(ethoxycarbonyl)-1-methyl-1H-pyrazol-3-yl]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022706Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])C.[Cl:9][C:10]1[CH:11]=[C:12]([C@@H:17]2[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][C@H:18]2[CH2:31][C:32](=O)[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:13]=[CH:14][C:15]=1[Cl:16].C[NH:41]N>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[C:12]([C@@H:17]2[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:19][C@H:18]2[CH2:31][C:32]2[C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:3][N:4]([CH3:6])[N:41]=2)[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

Conditions

Temperature: 80 °C

Procedure

N,N-Dimethylformamide dimethyl acetal (0.210 mL, 1.58 mmol) was added to a solution of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-(4-ethoxy-2,4-dioxobutyl)-1,4-oxazepane-4-carboxylate (500 mg, 1.05 mmol) in toluene (5 mL), and the mixture was stirred at 80° C. for 2 hr, and concentrated under reduced pressure. The residue was dissolved in ethanol (5 mL), and methylhydrazine (0.062 mL, 1.16 mmol) was added. The reaction mixture was stirred at 80° C. for 1.5 hr, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (175 mg).

Workup

concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in ethanol (5 mL)
stirringThe reaction mixture was stirred at 80° C. for 1.5 hr
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-537fc123c3e64b159cf595a97744cb07
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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