Benzaldehyde → N-benzyl-serine benzyl ester

HRID 12188Notes

Reaction equation

HRID 12188 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:15])[C@H:11]([CH2:13][OH:14])[NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CO>[CH2:2]([O:9][C:10](=[O:15])[C@H:11]([CH2:13][OH:14])[NH:12][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 12930233Benzyl L-serinate--hydrogen chloride (1/1)

Product 1

HCID 59337568N-benzyl-serine benzyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of L-serine-benzyl ester-HCl (2.3 g), benzaldehyde(1.05 eq.) and sodium acetate (1 eq.) in methanol was added sodium cyanoborohydride (1.0 eq.). The resulting mixture was stirred at ambient temperature for 15 hrs, then partitioned into ether and aqueous saturated sodium bicarbonate. The separated organic phase was extracted with 1M HCl (3×). Combined aqueous extracts were washed with ether, basified with aqueous 4.5M K2CO3 and extracted with ether. Combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to dryness to give 2.32 g of the desired compound (waxy solid, 81% yield).

Workup

  1. custompartitioned into ether and aqueous saturated sodium bicarbonate
  2. extractionThe separated organic phase was extracted with 1M HCl (3×)
  3. washCombined aqueous extracts were washed with ether
  4. extractionextracted with ether
  5. washCombined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d46c8f0fc93a42c984faa43c8c9ef0d6
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Reaction notes

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