Isobutyraldehyde → HCID 68930974, compound

HRID 32095Notes

Reaction equation

HRID 32095 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([NH:14][C:15](=[O:38])[CH2:16][CH:17]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)(=[O:21])=[O:20])[CH2:9][CH2:10][O:11]2)=[CH:6][CH:5]=1.[CH:39](=O)[CH:40]([CH3:42])[CH3:41].[BH4-].[Na+]>C(Cl)Cl.CC(O)=O>[CH2:39]([N:1]([CH2:3][CH:4]([CH3:13])[CH3:5])[CH2:2][CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([NH:14][C:15](=[O:38])[CH2:16][CH:17]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=3)(=[O:21])=[O:20])[CH2:9][CH2:10][O:11]2)=[CH:6][CH:5]=1)[CH:40]([CH3:42])[CH3:41]

Participants

6

Reactant 3

HCID 6561IsobutyraldehydeHCID 4311764Sodium borohydrideHCID 68929539n-[7-(2-Aminoethyl)-chroman-4-yl]-3-phenyl-3-(3-trifluoromethylbenzenesulfonylamino)-propionamide

Product 1

HCID 68930974HCID 68930974, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[7-(2-aminoethyl)-chroman-4-yl]-3-phenyl-3-(3-trifluoromethylbenzenesulfonylamino)-propionamide (Example 208, 50 mg, 0.09 mmol) in dry CH2Cl2 (8 mL) was added isobutyraldehyde (83 L, 0.9 mmol) and HOAc (1 drop). The resulting mixture was stirred at RT under N2 After 3 h, MS showed the formation of imine; NaBH4 (17 mg, 0.45 mmol) was then added. The resulting mixture was stirred for 18 h. Quenched with minimum amount of sat. NaHCO3. The organic layer was isolated, dried over MgSO4 and evaporated in vacuo. The crude product was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH mixture (97:3) gave final compound. MS m/z: 660.31 (M+H). Calc'd. for Calc'd. for C35H44F3N3O4S-659.82.

Workup

  1. stirringThe resulting mixture was stirred for 18 h
  2. customQuenched with minimum amount of sat. NaHCO3
  3. customThe organic layer was isolated
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe crude product was purified by chromatography on silica gel
  7. washElution with CH2Cl2

Sources & evidence

ORD record
ord-b3232069b3924d23ae2ae225d2d9db74
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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