Azide → HCID 59485944, compound

HRID 1972204Notes

Reaction equation

HRID 1972204 reaction equation
C(OC[C@@H]1OC(=O)N(C2C=CC(Cl)=CC=2)[C@H]1C1C=CC=C(C(F)(F)F)C=1)C1C=CC=CC=1.[N:33]([CH2:36][C@@H:37]1[O:41][C:40](=[O:42])[N:39]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=2)[C@H:38]1[C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=1)=[N+:34]=[N-:35].[N-]=[N+]=[N-].[F:63][C:64]1[CH:65]=[C:66]([C:70]#[CH:71])[CH:67]=[CH:68][CH:69]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)(C)(C)C.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:49][C:46]1[CH:45]=[CH:44][C:43]([N:39]2[C@@H:38]([C:50]3[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=3)[C@H:37]([CH2:36][N:33]3[CH:71]=[C:70]([C:66]4[CH:67]=[CH:68][CH:69]=[C:64]([F:63])[CH:65]=4)[N:35]=[N:34]3)[O:41][C:40]2=[O:42])=[CH:48][CH:47]=1

Participants

8

Reactant 5

HCID 33558AzideHCID 5202181-Ethynyl-3-fluorobenzeneHCID 23667548Sodium AscorbateHCID 59485955HCID 59485955, compoundHCID 86645367HCID 86645367, compound

Product 1

HCID 59485944HCID 59485944, compound

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

(4S,5R)-3-(4-chlorophenyl)-4-(3-(trifluoromethyl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one (from Example 72) was converted into (4S,5S)-5-(azidomethyl)-3-(4-chlorophenyl)-4-(3-(trifluoromethyl)phenyl)oxazolidin-2-one as described in Example 34. The azide (0.076 mmol) was then dissolved in t-butanol:water (2:1, 0.5 mL) and treated with 3-fluorophenylacetylene (0.076 mmol), followed by copper (II) sulfate pentahydrate (0.4 mg) and sodium ascorbate (0.75 mg). After stirring for 2 h, the reaction mixture was quenched with water and extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated. Purification on silica gel (30% ethyl acetate/hexanes) gave the title compound as a colorless oil. 1H NMR (acetone-d6) δ (ppm) 8.57 (s, 1H), 7.88 (s, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.72-7.70 (m, 2H), 7.67-7.63 (m, 2H), 7.50-7.44 (m, 3H), 7.30-7.28 (m, 2H), 7.11 (td, J=8.5, 2.3 Hz, 1H), 5.81 (d, J=5.2 Hz, 1H), 5.22-5.16 (m, 2H), 5.07 (ddd, J=5.5, 5.5, 4.4 Hz, 1H), 4.73-4.64 (m, 3H), 4.01 (d, J=3.6 Hz, 2H); HPLC-MS calculated C25H17ClF4N4O2 (M+H+): 517.1, found: 517.1.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on silica gel (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-81518e74d08f46e49bce1129b877d7cf
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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