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Trifluoroacetic acid → HCID 86719965, compound

HRID 532254
Notes
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Reaction equation

HRID 532254 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([NH:16][NH:17][C:18]([C@H:20]2[CH2:26][CH2:25][C@@H:24]3[CH2:27][N:21]2[C:22](=[O:33])[N:23]3[O:28][CH2:29][C:30]([OH:32])=[O:31])=[O:19])=[O:15])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[O:33]=[C:22]1[N:21]2[CH2:27][C@@H:24]([CH2:25][CH2:26][C@@H:20]2[C:18]([NH:17][NH:16][C:14]([C@@H:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[O:15])=[O:19])[N:23]1[O:28][CH2:29][C:30]([OH:32])=[O:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86719963trans-3-{N'-(6-carboxymethoxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl}-(R)-piperidin-1-carboxylic acid tert-butyl ester

Product 1

HCID 86719965HCID 86719965, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a clear solution of trans-3-{N′-(6-carboxymethoxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl}-(R)-piperidin-1-carboxylic acid tert-butyl ester (150 mg, 0.32 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid under stirring at −10° C. The reaction mixture was stirred for about 1 hour at −10° C. and the solvents were evaporated under vacuum to provide a residue. The residue was triturated successively with diethyl ether (25 ml) and acetonitrile (25 ml) and solvents were decanted to provide solid that was dried under vacuum to provide 59 mg of titled compound in 50% yield.

Workup

  1. stirringThe reaction mixture was stirred for about 1 hour at −10° C.
  2. customthe solvents were evaporated under vacuum
  3. customto provide a residue
  4. customThe residue was triturated successively with diethyl ether (25 ml) and acetonitrile (25 ml) and solvents
  5. customwere decanted
  6. customto provide solid
  7. customthat was dried under vacuum

Sources & evidence

ORD record
ord-4efc7171c0ce4caebfb652f8ff58b194
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853197B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes