Methanesulfonyl chloride → N-[(3S)-1-[2-fluoro-4-[(5S)-5-[(isoxazol-3-ylamino)methyl]-2-oxo-oxazolidin-3-yl]phenyl]pyrrolidin-3-yl]methanesulfonamide

HRID 8164Notes

Reaction equation

HRID 8164 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([NH:6][CH2:7][C@@H:8]2[O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:24][CH2:23][C@H:22]([NH:25]C(=O)C)[CH2:21]4)=[C:16]([F:29])[CH:15]=3)[CH2:9]2)=[N:2]1.Cl.N[C@H]1CCN(C2C=CC(N3C[C@H](CN(C4C=CON=4)C(OCC(Cl)(Cl)Cl)=O)OC3=O)=CC=2F)C1.[CH3:65][S:66](Cl)(=[O:68])=[O:67]>>[O:1]1[CH:5]=[CH:4][C:3]([NH:6][CH2:7][C@@H:8]2[O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:24][CH2:23][C@H:22]([NH:25][S:66]([CH3:65])(=[O:68])=[O:67])[CH2:21]4)=[C:16]([F:29])[CH:15]=3)[CH2:9]2)=[N:2]1

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 207257105(S)-Isoxazol-3-ylaminomethyl-3-(4-(3(S)-acetamidopyrrolidin-1-yl)-3-fluorophenyl)oxazolidin-2-oneHCID 69584925HCID 69584925, compound

Product 1

HCID 497429N-[(3S)-1-[2-fluoro-4-[(5S)-5-[(isoxazol-3-ylamino)methyl]-2-oxo-oxazolidin-3-yl]phenyl]pyrrolidin-3-yl]methanesulfonamide

Procedure

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).

Sources & evidence

ORD record
ord-341b1e2140474ab1a8223849066386e1
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Reaction notes

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