Sodium Carbonate → HCID 46861600, compound

HRID 1753978Notes

Reaction equation

HRID 1753978 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[Cl-].[F:8][C:9]([F:27])([F:26])[O:10][C:11]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:12]=1[CH2:13][CH2:14][C:15]1([O:21]2)[CH2:20][CH2:19][NH2+:18][CH2:17][CH2:16]1.C([O:32][C:33](=[O:46])[CH2:34][N:35]1[N:39]=[N:38][C:37]([CH:40]2[O:44][N:43]=[C:42](Br)[CH2:41]2)=[N:36]1)(C)(C)C.[NH4+].[Cl-]>CC(O)(C)C.CC(OC)(C)C>[F:27][C:9]([F:8])([F:26])[O:10][C:11]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:12]=1[CH2:13][CH2:14][C:15]1([O:21]2)[CH2:16][CH2:17][N:18]([C:42]2[CH:41]=[C:40]([C:37]3[N:38]=[N:39][N:35]([CH2:34][C:33]([OH:46])=[O:32])[N:36]=3)[O:44][N:43]=2)[CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 58539823HCID 58539823, compound2×HCID 68755004HCID 68755004, compound2×

Product 1

HCID 46861600HCID 46861600, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
115 °C

Procedure

tert-Butyl (5-{3-[5-(trifluoromethoxy)-3,4-dihydro-1′H-spiro[chromene-2,4′-piperidin]-1′-yl]-4,5-dihydroisoxazol-5-yl}-2H-tetrazol-2-yl)acetate A suspension of dried Na2CO3 (694 mg, 6.55 mmol) in anhydrous t-BuOH was added 5-(trifluoromethoxy)-3,4-dihydrospiro[chromene-2,4′-piperidinium]chloride (848 mg, 2.62 mmol) (Intermediate 8) and tert-butyl[5-(3-bromo-4,5-dihydroisoxazol-5-yl)-2H-tetrazol-2-yl]acetate (725 mg, 2.183 mmol) (Intermediate 7). The mixture was directly heated to 115° C. for 24 h. The reaction mixture was diluted with MTBE, poured into aq. NH4Cl and extracted with EtOAc. The organic layer was washed with water and brine. The aqueous phases were back extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on SiO2 (50 g, gradient from 0 to 70% EtOAc/hexanes) to afford the title compound as a white solid. LC-MS: m/z=539.1 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. extractionThe aqueous phases were back extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on SiO2 (50 g, gradient from 0 to 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-deeeaa8b042f418cb053327216813296
Source dataset
uspto-grants-2015_10
Patent number
US09168248B2

Reaction notes

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