C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine → HCID 71525796, compound

HRID 1528204Notes

Reaction equation

CO[C:3]1[C:6](=[O:7])[C:5](=[O:8])[C:4]=1[NH:9][C:10]1[CH:11]=[C:12]([S:16]([N:19]2[CH2:23][CH2:22][CH2:21][C@@H:20]2[C:24]([O:26][CH3:27])=[O:25])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1.[CH3:28][C:29]1[O:33][C:32]([CH:34]([NH2:40])[C:35]2([CH3:39])[CH2:38][O:37][CH2:36]2)=[CH:31][CH:30]=1>C(O)C>[CH3:28][C:29]1[O:33][C:32]([CH:34]([NH:40][C:3]2[C:6](=[O:7])[C:5](=[O:8])[C:4]=2[NH:9][C:10]2[CH:11]=[C:12]([S:16]([N:19]3[CH2:23][CH2:22][CH2:21][C@@H:20]3[C:24]([O:26][CH3:27])=[O:25])(=[O:17])=[O:18])[CH:13]=[CH:14][CH:15]=2)[C:35]2([CH3:39])[CH2:36][O:37][CH2:38]2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 408.4 mg of methyl (R)-1-[3-(2-methoxy-3,4-dioxocyclobut-1-enylamino)benzenesulfonyl]pyrrolidine-2-carboxylate and 350 mg of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine in 30 ml of ethanol was heated at 60° C. overnight. The solvent was evaporated off and the residue was taken up with 50 ml of ethyl acetate and washed twice with a 1 M sodium hydrogen phosphate solution. The organic phase was dried over magnesium sulfate and evaporated. 432 mg of methyl (R)-1-[3-(2-{[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-3,4-dioxocyclobut-1-enylamino)benzenesulfonyl]pyrrolidine-2-carboxylate were obtained. Yield=79%.

Workup

customThe solvent was evaporated off
washwashed twice with a 1 M sodium hydrogen phosphate solution
dry with materialThe organic phase was dried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-d4bf8f1f89574a688389c44ba5c44aa7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090596B2

Reaction notes

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