Reaktion #8260

ord-341b1e2140474ab1a8223849066386e1

Reaktionsgleichung

CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1
intermediate
CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1
5(S)-Isoxazol-3-ylaminomethyl-3-(4-(3(S)-acetamidopyrrolidin-1-yl)-3-fluorophenyl)oxazolidin-2-one
Cl.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1
3-(4-(3(S)-aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt
CS(=O)(=O)Cl
methanesulfonyl chloride
→
CS(=O)(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1
desired product
CS(=O)(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1
5(S)-Isoxazol-3-ylaminomethyl-3-(4-(3(S)-methanesulfonamido-pyrrolidin-1-yl)-3-fluorophenyl)oxazolidin-2-one

Edukte

CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1
intermediate
CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1
5(S)-Isoxazol-3-ylaminomethyl-3-(4-(3(S)-acetamidopyrrolidin-1-yl)-3-fluorophenyl)oxazolidin-2-one
Cl.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1
3-(4-(3(S)-aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt
CS(=O)(=O)Cl
methanesulfonyl chloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using essentially the method for the intermediate of Example 12, starting from 3-(4-(3(S)-aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (400 mg, 0.74 mM) and methanesulfonyl chloride gave the desired product (361 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07087629B2uspto-grants-2006_08