2-Methoxyethyl chloroformate → 3-(4-(3(S)-(2-Methoxyethoxycarbonylamino)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

HRID 1582352Notes

Reaction equation

HRID 1582352 reaction equation
O1C=CC(NC[C@@H]2OC(=O)N(C3C=CC(N4CC[C@H](NC(=O)C)C4)=C(F)C=3)C2)=N1.Cl.[NH2:31][C@H:32]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:47][C@H:46]([CH2:48][N:49]([C:58]4[CH:62]=[CH:61][O:60][N:59]=4)C(OCC(Cl)(Cl)Cl)=O)[O:45][C:44]3=[O:63])=[CH:39][C:38]=2[F:64])[CH2:33]1.Cl[C:66]([O:68][CH2:69][CH2:70][O:71][CH3:72])=[O:67]>>[CH3:72][O:71][CH2:70][CH2:69][O:68][C:66]([NH:31][C@H:32]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:47][C@H:46]([CH2:48][NH:49][C:58]4[CH:62]=[CH:61][O:60][N:59]=4)[O:45][C:44]3=[O:63])=[CH:39][C:38]=2[F:64])[CH2:33]1)=[O:67]

Participants

4

Reactant 3

HCID 694002-Methoxyethyl chloroformateHCID 207257105(S)-Isoxazol-3-ylaminomethyl-3-(4-(3(S)-acetamidopyrrolidin-1-yl)-3-fluorophenyl)oxazolidin-2-oneHCID 69584925HCID 69584925, compound

Product 1

HCID 695848763-(4-(3(S)-(2-Methoxyethoxycarbonylamino)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-oneYield 130.5%

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 (419 mg, 0.73 mM) and 2-methoxyethyl chloroformate (450 mg, 3.27 mM) gave the title compound (442 mg ). NMR (DMSO-d6) δ: 1.82 (hextet, 1H); 2.09 (hextet, 1H); 3.13 (m, 1H); 3.23 (s, 3H); 3.27 (m, 1H); 3.39 (m, 1H); 3.46 (t overlapping m, 3H); 3.81 (dd overlapping m, 2H); 4.05 (m, 2H); 4.13 (m, 2H); 4.32 (m, 1H); 4.97 (d, 1H); 5.02 (m, 1H); 5.08 (d, 1H); 6.71 (t, 1H); 6.88 (d, 1H); 7.08 (dd, 1H); 7.34.(dd, 1H); 7.52 (d, 1H); 8.89 (d, 1H). MS (ESP): 638 (MH+) for C24H27FN5O8Cl3

Sources & evidence

ORD record
ord-b3a4041f60af49dd9e15a39ad70636c2
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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