Trifluoroacetic acid → 3-(4-(1-(3-Hydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

HRID 1582372

Reaction equation

HRID 1582372 reaction equation
[OH:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]([C:12]2[C:17]([F:18])=[CH:16][C:15]([N:19]3[CH2:23][C@H:22]([CH2:24][N:25]([C:33]4[CH:37]=[CH:36][O:35][N:34]=4)C(OC(C)(C)C)=O)[O:21][C:20]3=[O:38])=[CH:14][C:13]=2[F:39])=[CH:8][CH2:7]1)=[O:5].FC(F)(F)C(O)=O>ClCCl.O>[OH:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]([C:12]2[C:13]([F:39])=[CH:14][C:15]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:33]4[CH:37]=[CH:36][O:35][N:34]=4)[O:21][C:20]3=[O:38])=[CH:16][C:17]=2[F:18])=[CH:8][CH2:7]1)=[O:5]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 571925683-(4-(1-(3-Hydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

Product 1

HCID 698904443-(4-(1-(3-Hydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-oneYield 70.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-(4-(1-(3-Hydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (176 mg, 0.32 mM), was dissolved in dichloromethane (1 ml) and treated with trifluoroacetic acid (1 ml) at ambient temperature. After stirring for 10 minutes, the mixture was diluted with water (15 ml) and dichloromethane (15 ml), the organic layer separated, washed with water (2×15 ml), and dried (magnesium sulfate). Solvent was removed, and the residue triturated with diethyl ether to give the desired product (102 mg). NMR (DMSO-d6) δ: 2.20 (m, 1H); 2.28 (m, 1H); 2.48 (m overlapped by DMSO, 2H); 3.42 (br m overlapped by H2O, ˜4H); 3.55 (br m, ˜3H); 3.83 (t, 1H); 4.01 (m, 1H); 4.06 (m, 2H); 4.81 (m, 1H); 5.78 (s, 1H); 5.92 (s, 1H); 6.47 (br s, 1H); 7.26 (d, 2H); 8.31 (s, 1H). MS (ESP): 449 (MH+) for C21H22F2N4O5

Workup

  1. customthe organic layer separated
  2. washwashed with water (2×15 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customSolvent was removed
  5. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-40086570b4784eb787b5caaa667659a9
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Linked notes

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