Hydrochloric Acid → 3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloro-ethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

HRID 1582345Notes

Reaction equation

HRID 1582345 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][N:26]([C:35]4[CH:39]=[CH:38][O:37][N:36]=4)[C:27]([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28])[O:22][C:21]3=[O:40])=[CH:16][C:15]=2[F:41])[CH2:10]1)=O)(C)(C)C.Cl>ClCCl.C(O)C>[NH2:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][N:26]([C:35]4[CH:39]=[CH:38][O:37][N:36]=4)[C:27]([O:29][CH2:30][C:31]([Cl:34])([Cl:32])[Cl:33])=[O:28])[O:22][C:21]3=[O:40])=[CH:16][C:15]=2[F:41])[CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 695849353-(4-(3(S)-(t-Butoxycarbonyl)aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

Product 1

HCID 695849263-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloro-ethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-oneYield 110.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-(4-(3(S)-(t-Butoxycarbonyl)aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (1.03 g, 1.62 mM) was dissolved in dichloromethane (5 ml) under nitrogen and treated with a solution of hydrogen chloride in ethanol (3.8 M, 25 ml). After stirring 5 hours at ambient temperature, solvent was removed, and the residue evaporated repeatedly with portions of dichloromethane to give the hydrochloride salt of the desired product as a white foam (962 mg ). NMR (DMSO-d6) δ: 2.02 (hextet, 1H); 2.25 (hextet, 1H); 3.26 (dd, 1H); 3.42 (m overlapped by solvent, ˜1H); 3.53 (m, 2H); 3.84 (dd overlapping m, 2H); 4.15 (m, 2H); 4.35 (dd, 1H); 4.97 (d, 1H); 5.02 (m, 1H); 5.08 (d, 1H); 6.77 (t, 1H); 6.88 (d, 1H); 7.12 (dd, 1H); 7.39 (dd, 1H); 8.48 (br, 3H); 8.91 (d, 1H). (+1 proton for HCl salt). MS (ESP): 536 (MH+) for C20H21Cl3FN5O5

Workup

  1. customsolvent was removed
  2. customthe residue evaporated repeatedly with portions of dichloromethane

Sources & evidence

ORD record
ord-bac17f8a76bc4f519169281cdcfc4e7b
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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