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 1582347Notes

Reaction equation

HRID 1582347 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 ). NMR (DMSO-d6) δ: 1.87 (hextet, 1H); 2.19 (hextet, 1H); 2.97 (s, 3H); 3.20 (m, 1H); 3.30 (m, 1H); 3.37 (m, 1H); 3.54 (m overlapped by H2O, ˜1H); 3.83 (dd, 1H); 3.97 (dd, 1H); 4.13 (dd overlapping m, 2H); 4.36 (dd, 1H); 4.97 (d, 1H); 5.02 (m, 1H); 5.07 (d, 1H); 6.74 (t, 1H); 6.88 (d, 1H); 7.09 (dd, 1H); 7.36 (dd overlapping br, 2H); 8.89 (d, 1H). MS (ESP): 578 (MH+) for C21H23Cl3FN5O7S

Sources & evidence

ORD record
ord-d7210eeb0ce04587b4f37fed725d379e
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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