Dichloromethane → N-benzyl-O-benzyl-D-serinamide

HRID 534679

Reaction equation

HRID 534679 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.ClCCl.FC(F)(F)C(O)=O.[OH-].[Na+]>O>[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

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 7216909N-benzyl-O-benzyl-N2-Boc-D-serinamide

Product 1

HCID 67082833N-benzyl-O-benzyl-D-serinamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N-benzyl-O-benzyl-N2-Boc-D-serinamide (30 g) and dichloromethane (150 mL), trifluoroacetic acid (150 mL) was added. The solution was stirred for 2 hours at room temperature for completion of reaction. The solution was concentrated under vacuum to obtain solid which was dissolved in water. 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 layers washed with brine solution. Organic layer was concentrated under vacuum to obtain an oily residue solidify by n-Hexane to give 20 g of N-benzyl-O-benzyl-D-serinamide.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customto obtain solid which
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers washed with brine solution
  5. concentrationOrganic layer was concentrated under vacuum
  6. customto obtain an oily residue solidify by n-Hexane

Sources & evidence

ORD record
ord-be2f9f7a3be14f24980bc1a11043ee1e
Source dataset
uspto-grants-2014_10
Patent number
US08853439B2

Linked notes

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