Acetic Acid → HCID 86704614, compound

HRID 1508566Notes

Reaction equation

HRID 1508566 reaction equation
C([O:5][C:6](=[O:51])[C:7]([CH3:50])([CH3:49])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([C:17]2[C:18]([CH2:27][N:28]3[C@@H:32]([CH3:33])[C@@H:31]([C:34]4[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[C:36]([C:44]([F:47])([F:46])[F:45])[CH:35]=4)[O:30][C:29]3=[O:48])=[N:19][C:20]([N:23]3[CH2:26][CH2:25][CH2:24]3)=[CH:21][CH:22]=2)[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[K+].C(O)(=O)C>ClCCl.C(OCC)(=O)C>[N:23]1([C:20]2[N:19]=[C:18]([CH2:27][N:28]3[C@@H:32]([CH3:33])[C@@H:31]([C:34]4[CH:35]=[C:36]([C:44]([F:46])([F:45])[F:47])[CH:37]=[C:38]([C:40]([F:41])([F:43])[F:42])[CH:39]=4)[O:30][C:29]3=[O:48])[C:17]([C:11]3[CH:10]=[C:9]([CH2:8][C:7]([CH3:49])([CH3:50])[C:6]([OH:51])=[O:5])[CH:14]=[CH:13][C:12]=3[O:15][CH3:16])=[CH:22][CH:21]=2)[CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 56968734HCID 56968734, compound

Product 1

HCID 86704614HCID 86704614, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl3-{3-[6-azetidin-1-yl-2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyridin-3-yl]-4-methoxyphenyl}-2,2-dimethylpropanoate (48 mg, 0.067 mmol) was dissolved in dichloromethane (1 mL). TFA (0.1 mL, 1.298 mmol) was added and the reaction was stirred at room temperature for 4 hours. The reaction was then concentrated and the residue was dissolved in methanol (1 mL). 4M KOH (0.333 mL, 1.330 mmol) was added, and the reaction was stirred for 10 min. at room temperature. Next, acetic acid (0.076 mL, 1.330 mmol) was added. The reaction was diluted with ethyl acetate (10 mL), washed with water (2×8 mL) and brine (8 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by PTLC (50% ethyl acetate/hexanes) to afford 3-{3-[6-azetidin-1-yl-2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyridin-3-yl]-4-methoxyphenyl}-2,2-dimethylpropanoic acid. LCMS=666.2 (M+H)+. 1H NMR (CDCl3, 500 MHz) δ 7.85 (s, 1H), 7.74 (s, 2H), 7.29 (d, J=7.6 Hz, 1H), 7.12 (dd, J=8.3, 2.2 Hz, 1H), 7.10-6.90 (m, 1H), 6.85 (d, J=8.5 Hz, 1H), 6.25 (d, J=8.2 Hz, 1H), 5.80-5.55 (m, 1H), 4.76 (m, 2H), 4.20-3.80 (m, 5H), 3.73 (s, 3H), 2.82 (m, 2H), 2.42 (bs, 2H), 1.35-1.15 (m, 6H), 0.75-0.58 (m, 3H).

Workup

  1. concentrationThe reaction was then concentrated
  2. dissolutionthe residue was dissolved in methanol (1 mL)
  3. stirringthe reaction was stirred for 10 min. at room temperature
  4. washwashed with water (2×8 mL) and brine (8 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by PTLC (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-79b9fd715ede49818fe5ea0f40bba404
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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