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

HRID 534676Notes

Reaction equation

HRID 534676 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 89.2%

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 (20%) (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 0.33 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-b57a19902d65452bbd7bac77b1dc4171
Source dataset
uspto-grants-2014_10
Patent number
US08853439B2

Reaction notes

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