Carbon Dioxide → HCID 18510678, compound

HRID 1370273Notes

Reaction equation

HRID 1370273 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:11][C@@H:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH:21]([N:28](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)=[O:13])[O:9][N:8]=2)[CH:2]=1.C(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:28][CH:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:12]([CH:10]2[O:9][N:8]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:11]2)=[O:13])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 516892Sodium BicarbonateHCID 86590907HCID 86590907, compound

Product 1

HCID 18510678HCID 18510678, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

) (50 ml) was added dropwise to a solution of 1,1-dimethylethyl (5S)-[[4-[[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]carbonyl]amino]phenyl]phenylmethyl][(1,1-dimethylethoxy)carbonyl]carbamate (0.0233 mol) in CH2Cl2 (500 ml), stirred at RT (CO2 gas evolution). The reaction mixture was stirred for 48 hours at RT. The reaction mixture was added dropwise to a saturated aqueous NaHCO3 solution, and this mixture was extracted with CH2Cl2. The separated organic layer was dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The residue was purified by short column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 97.5/2.5). The desired fractions were collected and the solvent was evaporated under reduced pressure. The resultant oil was stirred in EtOAc, filtered off, washed with EtOAc and DIPE, then dried, yielding 2.5 g (30%) of (±)-N-[4-(aminophenylmethyl) phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide (compound 502).

Workup

  1. extractionthis mixture was extracted with CH2Cl2
  2. dry with materialThe separated organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified by short column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 97.5/2.5)
  6. customThe desired fractions were collected
  7. customthe solvent was evaporated under reduced pressure
  8. stirringThe resultant oil was stirred in EtOAc
  9. filtrationfiltered off
  10. washwashed with EtOAc and DIPE
  11. customdried

Sources & evidence

ORD record
ord-61da7dab92a64c67a3680a689cbf33b9
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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