[1,3′-Biazetidine]-1′-carboxylic acid, 3-hydroxy-, 1,1-dimethylethyl ester → HCID 59605518, compound

HRID 1945525Notes

Reaction equation

HRID 1945525 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:15][CH:14]([OH:16])[CH2:13]2)[CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[N:12]1([CH:10]2[CH2:11][NH:8][CH2:9]2)[CH2:15][CH:14]([OH:16])[CH2:13]1

Participants

3

Reactant 1

HCID 59605880[1,3′-Biazetidine]-1′-carboxylic acid, 3-hydroxy-, 1,1-dimethylethyl ester

Product 1

HCID 59605518HCID 59605518, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A 25 mL round-bottomed flask was charged with a solution of 3-hydroxy-[1,3′]biazetidinyl-1′-carboxylic acid tert-butyl ester (0.69 g, 3.05 mmol) in DCM/TFA (4 mL/4 mL). The reaction mixture was stirred for 30 min at room temperature. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH to give [1,3′]Biazetidinyl-3-ol as a colourless oil (0.225 g, 58%). LCMS (Method A): RT=0.29 min, [M+H]+ 288.9

Workup

  1. washThe cartridge was washed with MeOH
  2. washthe desired product was eluted

Sources & evidence

ORD record
ord-11c161d5540e4b3b87cb6a3d1b512d2a
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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