Acetonitrile → HCID 57431014, compound

HRID 1670375Notes

Reaction equation

HRID 1670375 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16](=[O:23])[CH2:17][O:18][CH2:19][C:20]([OH:22])=[O:21])=[N+]=[N-].C(#N)C>O.[Pd]>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16](=[O:23])[CH2:17][O:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 713579901-Azido-13-oxo-3,6,9,15-tetraoxa-12-azaheptadecan-17-oic acid

Product 1

HCID 57431014HCID 57431014, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

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.

Workup

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

Sources & evidence

ORD record
ord-fe269cb41efe43d1afa802826f670305
Source dataset
uspto-grants-2011_08
Patent number
US07994134B2

Reaction notes

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