Trifluoroacetic acid → HCID 71724591, compound

HRID 2400741Notes

Reaction equation

HRID 2400741 reaction equation
[O:1]=[C:2]1[N:8]2[CH2:9][C@H:4]([CH2:5][CH2:6][C@@H:7]2[C:10]([NH:12][NH:13][C:14]([CH:16]2[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)=[O:15])=[O:11])[N:3]1[O:27][S:28]([OH:31])(=[O:30])=[O:29].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:18]1[CH2:17][CH:16]([C:14]([NH:13][NH:12][C:10]([C@H:7]2[CH2:6][CH2:5][C@H:4]3[CH2:9][N:8]2[C:2](=[O:1])[N:3]3[O:27][S:28]([OH:31])(=[O:30])=[O:29])=[O:11])=[O:15])[CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86694080HCID 86694080, compound

Product 1

HCID 71724591HCID 71724591, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution tert-butyl 3-[(2-{[(2R,5S)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}hydrazinyl)carbonyl]azetidine-1-carboxylate 262 (0.18 g, 0.39 mmol) in DCM (18 mL) was added trifluoroacetic acid (1.45 mL, 18.79 mmol) dropwise at 0° C. The reaction mixture was stirred for 1 h then evaporated. Ether was added to the residue and the resulting white precipitate was collected by centrifugation. The solid was triturated with a mixture of MeOH:ether (1:5, 6×) and the white solid was collected by centrifugation to give (2R,5S)—N′-(azetidin-3-ylcarbonyl)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide Compound 112 (Table 2) (0.04 g, 28%) as a white solid.

Workup

  1. customthen evaporated
  2. additionEther was added to the residue
  3. customthe resulting white precipitate was collected by centrifugation
  4. customThe solid was triturated with a mixture of MeOH:ether (1:5, 6×)
  5. customthe white solid was collected by centrifugation

Sources & evidence

ORD record
ord-580a4a1576384f7190cef6d9db0d4ca2
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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