HCID 90001511, compound → HCID 89996657, compound

HRID 2200832Notes

Reaction equation

HRID 2200832 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]([CH2:21][C:22]([O:24]CC1C=CC=CC=1)=[O:23])[CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl.CO.[Pd]>[C:16]([O:15][C:14]([NH:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][OH:1])[CH2:21][C:22]([OH:24])=[O:23])=[O:20])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 1

HCID 90001511HCID 90001511, compound

Product 1

HCID 89996657HCID 89996657, compoundYield 120.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethyl-[2-(2-hydroxyethoxyl)ethyl]amino]acetate (19) (1.25 g, 2.84 mmol) in DCM (4 mL) and methanol (6 mL) was added palladium (10%) on activated carbon (100 mg). The resulting mixture was placed under an atmosphere of hydrogen. The mixture was stirred at room temperature overnight and then filtered through Celite. The Celite was washed with methanol (2×20 mL) and the combined filtrates were concentrated at reduced pressure to give 1.20 g of 20. 13C NMR (CD3OD, 125 MHz) δ 170.5, 156.2, 79.3, 72.8, 70.6, 66.8, 61.4, 55.2, 55.0, 40.3, 28.5. ESMS (C15H31N2O7) [M+H]+ calc. 351.2131. found 351.2127.

Workup

  1. filtrationfiltered through Celite
  2. washThe Celite was washed with methanol (2×20 mL)
  3. concentrationthe combined filtrates were concentrated at reduced pressure

Sources & evidence

ORD record
ord-8e1ba84fbbc84e1d80719492df9751cf
Source dataset
uspto-grants-2016_06
Patent number
US09359392B2

Reaction notes

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