Triethylamine → HCID 178519140, compound

HRID 1944749Notes

Reaction equation

HRID 1944749 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19](O)=[O:20])[CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:24]1([C@H:30]2[CH2:34][O:33][C:32](=[O:35])[NH:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C>C1(C)C=CC=CC=1.Cl>[O:35]=[C:32]1[N:31]([C:19]([C@H:16]2[CH2:17][CH2:18][C@H:13]([NH:12][S:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:23])([F:1])[F:22])=[CH:8][CH:7]=3)(=[O:11])=[O:10])[CH2:14][CH2:15]2)=[O:20])[C@@H:30]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:34][O:33]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 7304242-Oxazolidinone, 4-phenyl-, (4S)-HCID 178525770HCID 178525770, compound2×

Product 1

HCID 178519140HCID 178519140, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of trans-4-(4-(trifluoromethyl)phenylsulfonamido)cyclohexanecarboxylic acid (Intermediate 18, 110 mg, 0.313 mmol,), (S)-4-phenyloxazolidin-2-one (25.5 mg, 0.157 mmol) in toluene (2 ml) was added triethylamine (0.087 ml, 0.626 mmol). The mixture was heated to 80° C. to obtain a solution. Pivaloyl chloride (0.039 ml, 0.313 mmol) in toluene (1 ml) was added to the reaction mixture, and it was heated to 110° C. with stirring for 18 hr. The reaction mixture was then diluted with 1M HCl and extracted with DCM. The DCM layer was dried (MgSO4), then filtered and concentrated in vacuo to a tanned solid. The crude material was purified via normal phase chromatography on biotage SP1, using 25+M column and a calculated gradient from 50% EtOAc in heptane, to yield the title compound as a white solid (8 mg, 10%). MS MH+ 497.2

Workup

  1. customto obtain a solution
  2. temperaturewas heated to 110° C.
  3. extractionextracted with DCM
  4. dry with materialThe DCM layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a tanned solid
  7. customThe crude material was purified via normal phase chromatography on biotage SP1

Sources & evidence

ORD record
ord-9ca3a89a17d34e75be60c27ac719aed7
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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