Trifluoroacetic acid → (2S, 5R)-6-sulfooxy-2-(aminomethyl)-7-oxo-1,6-diaza-bicyclo [3.2.1]octane

HRID 57336Notes

Reaction equation

HRID 57336 reaction equation
[Na:1].[S:2]([O:6][N:7]1[C:13](=[O:14])[N:12]2[CH2:15][C@H:8]1[CH2:9][CH2:10][C@H:11]2[CH2:16][NH:17]C(OC(C)(C)C)=O)([OH:5])(=[O:4])=[O:3].FC(F)(F)C(O)=O>ClCCl>[Na:1].[S:2]([O:6][N:7]1[C:13](=[O:14])[N:12]2[CH2:15][C@H:8]1[CH2:9][CH2:10][C@H:11]2[CH2:16][NH2:17])([OH:5])(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 5360545SodiumHCID 118016925(2S, 5R)-6-sulfooxy-2-(tert-butoxycarbonylaminomethyl)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane

Product 2

HCID 5360545SodiumHCID 91669185(2S, 5R)-6-sulfooxy-2-(aminomethyl)-7-oxo-1,6-diaza-bicyclo [3.2.1]octaneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

The sodium salt of (2S, 5R)-6-sulfooxy-2-(tert-butoxycarbonylaminomethyl)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane (2.4 g, 0.006 moles) was suspended in dichloromethane (6 ml) and to the reaction mixture was slowly added trifluoroacetic acid (6 ml) at about 0-5° C. The reaction mixture was stirred between about 0-5° C. for additional 2 hours. The solvent and excess trifluoroacetic acid was evaporated under vacuum below 40° C. to approximately ⅓ of its original volume to provide pale yellow oily residue. This oily residue was triturated with diethyl ether and ether was decanted (40 ml×2). The crude solid was again triturated with dichloromethane (40 ml×2) and solvents were decanted. The final solid was dried under vacuum below 40° C. to furnish 2.2 g of sodium and trifluoroacetic acid salt of (2S, 5R)-6-sulfooxy-2-(aminomethyl)-7-oxo-1,6-diaza-bicyclo [3.2.1]octane (X) (90% yield).

Workup

  1. customat about 0-5° C
  2. customThe solvent and excess trifluoroacetic acid was evaporated under vacuum below 40° C. to approximately ⅓ of its original volume
  3. customto provide pale yellow oily residue
  4. customThis oily residue was triturated with diethyl ether and ether
  5. customwas decanted (40 ml×2)
  6. customThe crude solid was again triturated with dichloromethane (40 ml×2) and solvents
  7. customwere decanted
  8. customThe final solid was dried under vacuum below 40° C.

Sources & evidence

ORD record
ord-f46b50065f3a406785e73a24ffcd5ceb
Source dataset
uspto-grants-2016_09
Patent number
US09434728B1

Reaction notes

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