Acetic Acid → H2N-PEG6-CH2COOtBu

HRID 1178171Notes

Reaction equation

HRID 1178171 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][N:26]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][NH2:26])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 10905931Azido-PEG6-C1-Boc

Product 1

HCID 11732002H2N-PEG6-CH2COOtBuYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 4 (1.0 g, 2.4 mmol) in ethanol (20 mL) was added 10% Pd/C (0.3 g) and acetic acid (0.3 mL). The resulting mixture was stirred under an atmosphere of hydrogen for 16 hours and then filtered to remove Pd/C. The filtrate was concentrated in vacuo and the residue was loaded onto a silica gel gravity column (100 g) and eluted with CH2Cl2:MeOH 20:1 to 10:1 (v/v) to afford compound 5 as a oil (0.90 g, 96%).

Workup

  1. filtrationfiltered
  2. customto remove Pd/C
  3. concentrationThe filtrate was concentrated in vacuo
  4. washeluted with CH2Cl2:MeOH 20:1 to 10:1 (v/v)

Sources & evidence

ORD record
ord-64dbb935e0b74bfcaf9e2a7621127afb
Source dataset
uspto-grants-2007_10
Patent number
US07276286B2

Reaction notes

Loading…