Hydrochloric Acid → N-benzyl-beta-benzyl-D-serinamide

HRID 534675

Reaction equation

HRID 534675 reaction equation
[CH2:1]([NH:8][C:9](=[O:28])[C@@H:10]([CH2:19][O:20]CC1C=CC=CC=1)[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>ClCCl>[CH2:1]([NH:8][C:9](=[O:28])[C@@H:10]([CH:19]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:20])[NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 7216909N-benzyl-O-benzyl-N2-Boc-D-serinamide

Product 1

HCID 86669435N-benzyl-beta-benzyl-D-serinamideYield 124.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzyl-O-benzyl-N2-Boc-D-serinamide (1 g) and dichloromethane (5 mL), aq.HCl (35%) (5 mL) was added. The solution was stirred for 2 hours at room temperature for completion of reaction. The solution was concentrated under vacuum to remove dichloromethane and subsequently water was added. The aqueous layer was basified to pH 8-10 with 5% sodium hydroxide. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with brine solution. Organic layer was concentrated under vacuum to obtain an oily residue 0.46 g of N-benzyl-β-benzyl-D-serinamide.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customto remove dichloromethane and subsequently water
  3. additionwas added
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layer was washed with brine solution
  6. concentrationOrganic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-c8d057bfa74a4821913f3d34508134d6
Source dataset
uspto-grants-2014_10
Patent number
US08853439B2

Linked notes

Loading…