Acetic Acid → HCID 12094117, compound

HRID 433128Notes

Reaction equation

HRID 433128 reaction equation
C(O)(=O)C.Br.C(OP([N:14]1[CH2:27][CH2:26][N:25]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N+:37]([O-:39])=[O:38])(=[O:30])=[O:29])[CH2:24][CH2:23][CH2:22][CH:21]([F:40])[CH2:20][CH2:19][CH2:18][N:17]([S:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[N+:50]([O-:52])=[O:51])(=[O:43])=[O:42])[CH2:16][CH2:15]1)(=O)OCC)C>C(OCC)C>[F:40][CH:21]1[CH2:22][CH2:23][CH2:24][N:25]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N+:37]([O-:39])=[O:38])(=[O:29])=[O:30])[CH2:26][CH2:27][NH:14][CH2:15][CH2:16][N:17]([S:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[N+:50]([O-:52])=[O:51])(=[O:42])=[O:43])[CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 46180616HCID 46180616, compound

Product 1

HCID 12094117HCID 12094117, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Acetic acid (15 ml), saturated with anhydrous hydrogen bromide (gas) was added to [11-fluoro-1,7-bis(2-nitro-benzenesulfonyl)-1,4,7-triaza-cyclotetradec-4-yl]-phosphonic acid diethyl ester (560 mg, 0.77 mmol) contained in round-bottomed flask closed by glass stopper. The resulting mixture was allowed to stir for 18 hours at room temperature and then diethyl ether (50 ml) was added. The white precipitate which formed was allowed to settle to the bottom of the flask and the diethyl ether solution was decanted off. This white solid was re-dissolved in methanol, stirred with K2CO3 (solid) for 30 mins then diluted with 100-ml ethyl acetate, and the solids were removed by filtration. Evaporation of the filtrates gave the title compound (454 mg, 100%) as white foam.

Workup

  1. customcontained in round-bottomed flask
  2. customclosed by glass stopper
  3. customThe white precipitate which formed
  4. customthe diethyl ether solution was decanted off
  5. dissolutionThis white solid was re-dissolved in methanol
  6. stirringstirred with K2CO3 (solid) for 30 mins
  7. additionthen diluted with 100-ml ethyl acetate
  8. customthe solids were removed by filtration
  9. customEvaporation of the filtrates

Sources & evidence

ORD record
ord-e97cd6b71b304b91ac99a1d17ef5f212
Source dataset
uspto-grants-2003_12
Patent number
US06667320B2

Reaction notes

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