HCID 90001626, compound → HCID 89996650, compound

HRID 2200829Notes

Reaction equation

HRID 2200829 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][N:14]([CH2:26][CH2:27][O:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:15][C:16]([O:18]CC1C=CC=CC=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:35]([O:34][C:32]([NH:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][N:14]([CH2:13][CH2:12][O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:15][C:16]([OH:18])=[O:17])=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

3

Reactant 1

HCID 90001626HCID 90001626, compound

Product 1

HCID 89996650HCID 89996650, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

A solution of benzyl 2-[bis[2-[2-(tert-butoxycarbonylamino)ethoxy]ethyl]amino]acetate (2) (2.2 g, 4.1 mmol) in methanol (70 mL) was degassed by bubbling argon through solution for five minutes. Palladium (10%) on activated carbon (220 mg) was added to the solution and the reaction mixture was placed under an atmosphere of hydrogen. The reaction was allowed to stir at 15° C. for 15 h before being filtered through a pad of Celite. The Celite was washed with methanol (2×20 mL) and the combined filtrates were concentrated at reduced pressure to provide a colourless oil (1.69 g, 3.8 mmol, 92%, >95% purity by HPLC). The product (4) was used without further purification. 13C NMR (CD3OD) δ170.1, 158.5, 80.2, 71.5, 65.9, 58.4, 55.8, 41.2, 28.8. ESMS (C20H39N3O8) [M+Na]+ calc. 472.2635. found 472.2623.

Workup

  1. customby bubbling argon through solution for five minutes
  2. additionPalladium (10%) on activated carbon (220 mg) was added to the solution
  3. filtrationbefore being filtered through a pad of Celite
  4. washThe Celite was washed with methanol (2×20 mL)
  5. concentrationthe combined filtrates were concentrated at reduced pressure
  6. customto provide a colourless oil (1.69 g, 3.8 mmol, 92%, >95% purity by HPLC)
  7. customThe product (4) was used without further purification

Sources & evidence

ORD record
ord-187aa3dee376401fa09c512cca392da0
Source dataset
uspto-grants-2016_06
Patent number
US09359392B2

Reaction notes

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