Acetic Acid → HCID 178516678, compound

HRID 1013840Notes

Reaction equation

HRID 1013840 reaction equation
C([C@@H]1CO[C:10](=O)[N:9]1[C:14](=[O:33])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([C:27]([F:30])([F:29])[F:28])=[C:22]([F:31])[C:21]=1[F:32])[CH2:16]C=O)C1C=CC=CC=1.[N:34]1[NH:35][CH:36]=[C:37]2[C:42]=1[CH2:41][CH2:40][CH:39](N)[CH2:38]2.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[Cl:26][C:25]1[C:20]([CH2:19][C@@H:15]2[CH2:16][CH2:10][N:9]([CH:39]3[CH2:40][CH2:41][C:42]4[C:37](=[CH:36][NH:35][N:34]=4)[CH2:38]3)[C:14]2=[O:33])=[C:21]([F:32])[C:22]([F:31])=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:24]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 86629986HCID 86629986, compoundHCID 178507369HCID 178507369, compound

Product 1

HCID 178516678HCID 178516678, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Combine a solution of (R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(6-chloro-2,3-difluoro-4-trifluoromethyl-benzyl)-4-oxo-butyraldehyde (Preparation 46) (0.30 g, 0.6 mmol) and 4,5,6,7-Tetrahydro-2H-indazol-5-ylamine (Preparation 40) (88 mg, 0.64 mmol) in CH2Cl2 (15 mL) and MeOH (1 mL) and treat the solution with HOAc (0.03 mL, 0.6 mmol). Stir the reaction for 30 min at room temperature, treat the reaction with sodium triacetoxyborohydride (0.39 g, 1.8 mmol), and stir overnight at room temperature. Quench the reaction with water and extract with EtOAc. Wash the organic with brine, dry over MgSO4, filter, and remove the solvent. Purify the crude by SCX resin exchange column using 2M ammonia in MeOH to elute the pure product. Remove the solvent to afford 0.12 g (46%) of the title compound. MS (m/e): 434 (M+1).

Workup

  1. customthe reaction for 30 min at room temperature
  2. additiontreat
  3. stirringstir overnight at room temperature
  4. customQuench
  5. customthe reaction with water
  6. extractionextract with EtOAc
  7. washWash the organic with brine
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. customremove the solvent
  11. customPurify the crude by SCX resin exchange column
  12. washto elute the pure product
  13. customRemove the solvent

Sources & evidence

ORD record
ord-43278a0470934bc2b544a0fa7aa4551a
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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