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

HRID 593254Notes

Reaction equation

HRID 593254 reaction equation
[CH2:1]([NH:8][C:9](=[O:28])[C@@H:10]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[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 67082833N-benzyl-O-benzyl-D-serinamideYield 30%

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 (10%) (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 was basified to pH 8-10 with 5% sodium hydroxide. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with brine solution. Organic layer was concentrated under vacuum to obtain an oily residue 0.22 g of N-benzyl-O-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 layers washed with brine solution
  6. concentrationOrganic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-4ada351de5c141edad701d7cc5f2d424
Source dataset
uspto-grants-2016_01
Patent number
US09242926B2

Reaction notes

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