Sodium Carbonate → HCID 86680330, compound

HRID 2360706Notes

Reaction equation

HRID 2360706 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Cl.[NH2:12][C@@H:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH3:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:19][O:18][C:16](=[O:17])[C@H:13]([NH:12][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312444-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 13283516methyl (2R)-2-aminobutanoate hydrochloride

Product 1

HCID 86680330HCID 86680330, compoundYield 107.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 g of p-methoxybenzaldehyde and 12.98 g of methyl D-homoalaninate-hydrochloride were dissolved in 160 ml of DCM and at 0° C. 11.35 ml of TEA were added. After 10 min at 0° C. 23.36 g of sodium triacetoxyborohydride were added in small portions. The reaction was stirred at r.t. overnight. To the reaction was then added aqueous sodium carbonate solution (10%). The layers were separated and the organic layer was washed with water until neutral, dried over Na2SO4, filtered and concentrated in vacuo. 18.72 g of the title compound were obtained and used without further purification.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water until neutral,
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-477da9993bf64f8588ed69125f70df53
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

Loading…