Triethylamine → HCID 178522111, compound

HRID 1846801Notes

Reaction equation

HRID 1846801 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH2:1]([O:8][C@H:9]1[CH2:10][C@H:11]([C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:15])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([O:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 128151113-(Benzyloxy)cyclobutane-1-carboxylic acid

Product 2

HCID 178522111HCID 178522111, compoundHCID 178522112HCID 178522112, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (2.21 g, 5.82 mmol) was added to a stirred mixture of 3-(benzyloxy)cyclobutanecarboxylic acid (0.80 g, 3.88 mmol), 2-aminopyridine (0.73 g, 7.76 mmol), and triethylamine (1.08 mL, 7.76 mmol) in DMF (15 mL). The reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was separated, washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified via silica gel chromatography to give the separated diastereomers trans-3-(benzyloxy)-N-(pyridin-2-yl)cyclobutanecarboxamide and cis-3-(benzyloxy)-N-(pyridin-2-yl)cyclobutanecarboxamide.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. customwas separated
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-4e58d97c43f44b56ac04db04a48a0a60
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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