Triethylamine → HCID 67172912, compound

HRID 1891257Notes

Reaction equation

HRID 1891257 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([Cl:10])[CH:3]=1.Cl.[CH3:12][O:13][C:14](=[O:17])[CH2:15][NH2:16].C(N(CC)CC)C.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:16][CH2:15][C:14]([O:13][CH3:12])=[O:17])=[C:4]([Cl:10])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 4311764Sodium borohydrideHCID 141091094-Bromo-2-chlorobenzaldehyde

Product 1

HCID 67172912HCID 67172912, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

4-bromo-2-chlorobenzaldehyde (2B1) (4.56 mmol, 1.0 g) and glycine methyl ester hydrochloride (2C2) (4.56 mmol, 572 mg) were dissolved in ethanol (15 ml) under nitrogen with stirring and triethylamine (135 mmol, 19.0 ml, 13.7 g) was added. The reaction mixture was heated to 50° C. for 1 hour, then evaporated to dryness and the residue taken up in methanol (15 ml) and cooled in an ice bath. Sodium borohydride (5.01 mmol, 0.190 g) was added portionwise and stirring continued until no starting material remained as determined by TLC. The reaction mixture was concentrated to dryness and partitioned between DCM and water and the phases separated. The organic layer was dried over sodium sulphate, filtered and concentrated before purification on silica eluting with 15% EtOAc/heptane to yield methyl 2-(4-bromo-2-chlorobenzylamino)acetate (2C3) 420 mg (31%); 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H) 7.38 (d, 1H) 7.31 (d, 1H) 3.86 (s, 2H) 3.73 (s, 3H) 3.43 (s, 2H).

Workup

  1. customevaporated to dryness
  2. temperaturecooled in an ice bath
  3. stirringstirring
  4. concentrationThe reaction mixture was concentrated to dryness
  5. custompartitioned between DCM and water
  6. customthe phases separated
  7. dry with materialThe organic layer was dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated before purification on silica eluting with 15% EtOAc/heptane

Sources & evidence

ORD record
ord-b5818a872bba402e9165be61fbd12517
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

Loading…