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

HRID 534674Notes

Reaction equation

HRID 534674 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 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N-benzyl-O-benzyl-N2-Boc-D-serinamide (16 g) and dichloromethane (80 mL), trifluoroacetic acid (80 mL) was added. The solution was stirred for 2 hours and the reaction was monitored for completion of reaction. The solution was concentrated under vacuum to obtain solid which was dissolved in water. The aqueous solution was basified to pH 8-10 with 5% sodium hydroxide and was extracted with ethyl acetate. The organic layer was separated and washed with a brine solution. The organic layer was concentrated under vacuum to obtain an oily residue 11 g of N-benzyl-O-benzyl-D-serinamide.

Workup

  1. customthe reaction was monitored for completion of reaction
  2. concentrationThe solution was concentrated under vacuum
  3. customto obtain solid which
  4. extractionwas extracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with a brine solution
  7. concentrationThe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-890a981e1f84428a901e3d86c71b343c
Source dataset
uspto-grants-2014_10
Patent number
US08853439B2

Reaction notes

Loading…