Trifluoroacetic acid → HCID 73386851, compound

HRID 330913Notes

Reaction equation

HRID 330913 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([O:12][NH:13][C:14]([C@@H:16]2[CH2:22][CH2:21][C@@H:20]3[CH2:23][N:17]2[C:18](=[O:29])[N:19]3[O:24][S:25]([O-:28])(=[O:27])=[O:26])=[O:15])[CH2:9]1)=O)(C)(C)C.C([N+](CCCC)(CCCC)CCCC)CCC.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH:10]([O:12][NH:13][C:14]([C@@H:16]2[CH2:22][CH2:21][C@@H:20]3[CH2:23][N:17]2[C:18](=[O:29])[N:19]3[O:24][S:25]([OH:28])(=[O:26])=[O:27])=[O:15])[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86699590HCID 86699590, compound

Product 1

HCID 73386851HCID 73386851, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N,N-tributylbutan-1-aminium ({[(2S,5R)-2-({[1-(tert-butoxycarbonyl)azetidin-3-yl]oxy}carbamoyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl]oxy}sulfonyl)oxidanide 40 (0.1 g, 0.15 mmol) in DCM (8.8 mL) was added trifluoroacetic acid (0.44 mL, 5.7 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 acetonitrile (2×) and the white solid was collected by centrifugation. The white solid was purified by HPLC and freeze-dried to give (2S,5R)—N-(azetidin-3-yloxy)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide Compound 8 (Table 1) (0.01 g, 20%) as a white solid.

Workup

  1. customevaporated
  2. additionEther was added to the residue
  3. customthe resulting white precipitate was collected by centrifugation
  4. customThe solid was triturated with acetonitrile (2×)
  5. customthe white solid was collected by centrifugation
  6. customThe white solid was purified by HPLC
  7. customfreeze-dried

Sources & evidence

ORD record
ord-cba7d7e2bb344fadaa0f50ed8373e2c7
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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