HCID 89939862, compound → HCID 89939902, compound

HRID 2205585Notes

Reaction equation

HRID 2205585 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[NH:15][CH:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 89939862HCID 89939862, compound

Product 1

HCID 89939902HCID 89939902, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 6-((tert-butoxycarbonylamino)methyl)picolinate (8.74 g, 31.2 mmol) was dissolved in AcOH and degassed with argon in a reactor (Roth), then catalytical amount PtO2 was added and degassed with argon again. The reaction was stirred at room temperature under H2 (40 bar) for 3 days. 8a was not fully converted. The reaction mixture was filtered through celite, concentrated in vacuo and purified with flash chromatography in EE. The retrieval of 8a was repeated until 100% converted with the same procedure.

Workup

  1. customdegassed with argon in a reactor (Roth)
  2. additioncatalytical amount PtO2 was added
  3. customdegassed with argon again
  4. filtrationThe reaction mixture was filtered through celite
  5. concentrationconcentrated in vacuo
  6. custompurified with flash chromatography in EE

Sources & evidence

ORD record
ord-24e0ce9766704c349901fe58de8bd997
Source dataset
uspto-grants-2016_06
Patent number
US09371322B2

Reaction notes

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