HCID 578300, compound → HCID 43377937, compound

HRID 2175309Notes

Reaction equation

HRID 2175309 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=O)[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]>C1COCC1>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

3

Reactant 1

HCID 578300HCID 578300, compound

Product 1

HCID 43377937HCID 43377937, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a partial suspension of methyl 4-(2,3-dimethylphenylamino)-4-oxobutanoate (0.20 g, 0.85 mmol) in THF (8.5 mL) at 0° C. was added 1 M borane tetrahydrofuran complex (2.55 mL, 2.55 mmol) over 2 min. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was cautiously quenched with 50% saturated ammonium chloride, and then excess 50% saturated ammonium chloride and DCM were added. The resulting mixture was stirred vigorously for 15 min. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated. The residue was purified by preparative HPLC (PHENOMENEX® Axia Luna column, 5μ, C18, 30×75 mm; 15 min gradient from 100% A: 0% B to 0% A:100% B and 3 min 100% B (A=90% H2O/10% MeCN+0.1% TFA); (B=90% MeCN/10% H2O+0.1% TFA); detection at 220 nm) to afford the title compound (85 mg, 45% yield). LCMS, [M+H]+=222.1.

Workup

  1. additionwas added 1 M borane tetrahydrofuran complex (2.55 mL, 2.55 mmol) over 2 min
  2. customThe reaction was cautiously quenched with 50% saturated ammonium chloride
  3. additionexcess 50% saturated ammonium chloride and DCM were added
  4. stirringThe resulting mixture was stirred vigorously for 15 min
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by preparative HPLC (PHENOMENEX® Axia Luna column
  10. custom15 min gradient
  11. custom100% B and 3 min 100% B

Sources & evidence

ORD record
ord-a7f47407ef5a40ad87941984cdea7bb5
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

Loading…