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Trifluoroacetic acid → HCID 89726033, compound

HRID 592067
Notes
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Reaction equation

HRID 592067 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:6][CH2:5][N:4]([C:7]([O:9]C(C)(C)C)=O)[CH2:3][CH:2]1[C:14]([O:16]C)=[O:15].C(O)(C(F)(F)F)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[CH:63]([C:65]1[CH:66]=[C:67]([CH:71]=[CH:72][CH:73]=1)C(O)=O)=[O:64].[OH-].[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CO>[CH:63]([C:65]1[CH:73]=[C:72]([CH:71]=[CH:67][CH:66]=1)[C:7]([N:4]1[CH2:5][CH2:6][NH:1][CH:2]([C:14]([OH:16])=[O:15])[CH2:3]1)=[O:9])=[O:64]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 120773-CarboxybenzaldehydeHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 224585731,4-Di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate

Product 1

HCID 89726033HCID 89726033, compoundYield 100.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1,4-di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate 29 (1.0 g, 2.9 mmol) in DCM (20 mL) was added TFA (2.31 g, 20.3 mmol) at 0° C. The reaction mixture was stirred at RT for 4 h. TLC analysis indicated complete conversion of SM. Reaction was concentrated to remove excess of TFA and sticky solid so obtained was taken in DCM (20 mL). To this suspension, HATU (1.65 g, 4.34 mmol), NMM (293 mg, 2.9 mmol), 3-formylbenzoic acid (435 mg, 2.9 mmol), and DMAP (10 mg) were added. Reaction mixture was stirred at RT for 16 h. The reaction was monitored by LCMS. The reaction mixture was diluted with DCM and washed with water; organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The sticky solid so obtained was added to a solution of NaOH (65 mg, 1.6 mmol) in MeOH (5 mL). Reaction mixture was stirred at rt for 7 h. The reaction was monitored by TLC. When SM was completely consumed, reaction mixture was concentrated under vacuum. The solid was suspended in water and acidified to pH 6 using 1 N HCl. The suspension was filtered and the precipitate was triturated with ethanol to give 766 mg (20%) of 4-(3-formylbenzoyl)piperazine-2-carboxylic acid 32 as sticky solid.

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. customto remove excess of TFA and sticky solid
  4. customso obtained
  5. customReaction mixture
  6. stirringwas stirred at RT for 16 h
  7. washwashed with water
  8. customorganic layer was separated
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure
  11. customThe sticky solid so obtained
  12. customReaction mixture
  13. stirringwas stirred at rt for 7 h
  14. customWhen SM was completely consumed
  15. customreaction mixture
  16. concentrationwas concentrated under vacuum
  17. filtrationThe suspension was filtered
  18. customthe precipitate was triturated with ethanol

Sources & evidence

ORD record
ord-e35ea073a762484baee916053c96c33f
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238656B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes