Sodium Chloride → Methyl (2-((tert-butoxycarbonyl)amino)ethyl)glycinate

HRID 841141Notes

Reaction equation

HRID 841141 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].[Cl-].[Na+]>C(Cl)Cl>[CH3:24][O:23][C:21](=[O:22])[CH2:20][NH:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:11]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 187201N-BOC-ethylenediamine

Product 1

HCID 10889780Methyl (2-((tert-butoxycarbonyl)amino)ethyl)glycinateYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-aminoethyl)carbamic acid tert-butyl ester (from Step 6 below) (4.2 g, 26.3 mmol) in methylene chloride (50 mL) was added triethylamine (4.4 mL, 31.4 mmol) and methyl bromoacetate (2.4 mL, 26.3 mmol). The reaction was stirred overnight at room temperature. A saturated aqueous solution of sodium chloride (100 mL) was then added, and the organic layer was separated dried over MgSO4, filtered and concentrated. The residue was taken up in diethyl ether, and a saturated solution of HCl in diethyl ether was added to precipitate the product, which was filtered, and dried. It was recrystallized in ethanol/ethyl acetate, to give a white solid; 1.39 g (20% yield). MS-APCI: M+1=233.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additiona saturated solution of HCl in diethyl ether was added
  6. customto precipitate the product, which
  7. filtrationwas filtered
  8. customdried
  9. customIt was recrystallized in ethanol/ethyl acetate
  10. customto give a white solid

Sources & evidence

ORD record
ord-acfc809c7b4241f2bb0ea22a05d3bb2a
Source dataset
uspto-grants-2002_04
Patent number
US06369034B1

Reaction notes

Loading…