1-Boc-Azetidine-3-carboxylic acid → HCID 86702385, compound

HRID 1851244Notes

Reaction equation

HRID 1851244 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1NC=CN=1)(C1NC=CN=1)=O.[CH3:27][C:28]1[N:33]=[C:32]([C:34](=[N:36][NH2:37])[NH2:35])[CH:31]=[CH:30][CH:29]=1>ClCCl>[NH2:35][C:34]([C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:27])[N:33]=1)=[N:36][NH:37][C:12]([CH:10]1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:11]1)=[O:14]

Participants

5

Reactant 3

HCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 573576606-Methylpyridine-2-carbohydrazonamide

Product 1

HCID 86702385HCID 86702385, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8.21 g (54.7 mmol) 1-(tert-butoxycarbonyl) azetidine-3-carboxylic acid in 80 mL dichloromethane are added 8.86 g (54.7 mmol) carbonyl diimidazole within 30 min. After stirring for five minutes 11 g (54.7 mmol) 6-methylpyridine-2-carbohydrazonamide are added and the reaction mixture is stirred at room temperature for 3 hours. The solvent has been evaporated and the residue is treated with water. The formed precipitate has been filtered off and dried yielding 16.47 g (81.3%) of the desired compound as a mixture of tautomers.

Workup

  1. additionare added
  2. customThe solvent has been evaporated
  3. additionthe residue is treated with water
  4. filtrationThe formed precipitate has been filtered off
  5. customdried

Sources & evidence

ORD record
ord-06f3c10fbcd84ab89b644dd99746e39a
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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