Acetic Acid → HCID 18449409, compound

HRID 1270409Notes

Reaction equation

HRID 1270409 reaction equation
C=O.[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10]1([C:18](=[O:19])[NH:17][C:16](=[O:20])[NH:15]1)[CH2:9]2)([O-])=O.[CH3:21]C(O)=O.C([BH3-])#N.[Na+]>CO.C1COCC1>[CH3:21][NH:3][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10]1([C:18](=[O:19])[NH:17][C:16](=[O:20])[NH:15]1)[CH2:9]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 16638331HCID 16638331, compound2×

Product 1

HCID 18449409HCID 18449409, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of formaldehyde (0.026 mL of a 37 wt % aqueous solution, 0.32 mmol), (±)-5′-amino-spiro[imidazolidine-4,2′-indane]-2,5-dione (described in Intermediate 45) (50 mg, 0.23 mmol), and AcOH (0.053 mL, 0.92 mmol) in MeOH (3 mL) at ambient temperature was added sodium cyanoborohydride (0.34 mL of a 1 M solution in THF, 0.34 mmol) and the reaction mixture was stirred for 4 h, then concentrated ill vacuo. The residue was partioned between saturated aqueous NaHCO3 and EtOAc. The organic layer was removed, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound as an off-white solid. MS: m/z=232 (M+1).

Workup

  1. concentrationconcentrated ill vacuo
  2. customThe organic layer was removed
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by HPLC
  7. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-eeadaa985bfa412b8d864cf2bcd72a9b
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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