3-(4-(3(S)-(2(S),3-Dihydroxypropanoyl)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one → HCID 69889576, compound

HRID 1582367Notes

Reaction equation

[OH:1][C@@H:2]([CH2:30][OH:31])[C:3]([C@H]1CCN(C2C=CC(N3C[C@H](CNC4C=CON=4)OC3=O)=CC=2F)C1)=[O:4].Cl.[NH:33]1[CH2:38][CH2:37][C:36]([C:39]2[C:44]([F:45])=[CH:43][C:42]([N:46]3[CH2:50][C@H:49]([CH2:51][N:52]([C:60]4[CH:64]=[N:63][S:62][N:61]=4)C(OC(C)(C)C)=O)[O:48][C:47]3=[O:65])=[CH:41][C:40]=2[F:66])=[CH:35][CH2:34]1>>[OH:1][C@@H:2]([CH2:30][OH:31])[C:3]([N:33]1[CH2:38][CH2:37][C:36]([C:39]2[C:40]([F:66])=[CH:41][C:42]([N:46]3[CH2:50][C@H:49]([CH2:51][NH:52][C:60]4[CH:64]=[N:63][S:62][N:61]=4)[O:48][C:47]3=[O:65])=[CH:43][C:44]=2[F:45])=[CH:35][CH2:34]1)=[O:4]

Participants

Reactant 2

HCID 537427063-(4-(3(S)-(2(S),3-Dihydroxypropanoyl)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

HCID 69584729HCID 69584729, compound

Product 1

HCID 69889576HCID 69889576, compoundYield 71%

Procedure

Using the method described for the appropriate intermediate of Example 17, apart from routine changes in the eluant used for chromatography, and starting from 3-(4-(1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-(N-(t-butoxycarbonyl)-1,2,5-thiadiazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride (800 mg, 1.51 mM, see Example 25), gave the title product (669 mg, 71%). NMR (DMSO-d6) δ: 1.29 (s, 3H); 1.32 (s, 3H); 1.52 (s, 9H); 2.30 (m, 1H); 2.40 (m, 1H); 3.68 (m, 2H); 3.90 (dd, 1H); 4.04-4.28 (m, 4H); 4.37 (m, 1H); 4.90 (m, 1H); 5.06 (m, 1H); 5.72 (m, 2H); 5.88 (m, 1H); 7.31 (d, 2H); 8.96 (s, 1H). MS (ESP): 622 (MH+) for C28H33F2N5O7S

Sources & evidence

ORD record: ord-1820022fcdb745639ec0871eff343930
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734200B1

Reaction notes

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