Reaction #969842

ord-7c969521af6f462a93f648190c33640d

Reaction equation

[N-]=[N+]=NCCOCCOCCOCCNC(=O)COCC(=O)O
17-azido-5-oxo-6-aza-3,9,12,15-tetraoxaheptadecanoic acid
CC#N
acetonitrile
→
NCCOCCOCCOCCNC(=O)COCC(=O)O
17-Amino-5-oxo-6-aza-3,9,12,15-tetraoxaheptadecanoic acid

Reactants

[N-]=[N+]=NCCOCCOCCOCCNC(=O)COCC(=O)O
17-azido-5-oxo-6-aza-3,9,12,15-tetraoxaheptadecanoic acid
—
H2(g)-Pd/C
CC#N
acetonitrile

Reagents

None

Solvents

O
water
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherUV detection at 214 and 284 nm, ES ionisation giving M+H at 335
  2. 2
    FiltrationThe solution was filtered

Procedure

A solution of 17-azido-5-oxo-6-aza-3,9,12,15-tetraoxaheptadecanoic acid (8.36 g, 25.0 mmol) in water (100 ml) was reduced using H2(g)-Pd/C (10%). The reaction was run until LC-MS analysis showed complete conversion of starting material (column Vydac 218TP54; solvents: A=water/0.1% TFA and B=acetonitrile/0.1% TFA; gradient 4-16% B over 20 min; flow 1.0 ml/min; UV detection at 214 and 284 nm, ES ionisation giving M+H at 335 for starting material and 309 for the product). The solution was filtered and used directly in the next step.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08236283B2uspto-grants-2012_08