Benzoic Acid → HCID 58375026, compound

HRID 536682Notes

Reaction equation

HRID 536682 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[C:47]([OH:55])(=O)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(N(C(C)C)C(C)C)C.[CH3:65][C@:66]12[C:74]([CH3:76])([CH3:75])[C@H:70]([NH:71][CH2:72][CH2:73]1)[CH2:69][C:68]1[C:77]([OH:81])=[CH:78][CH:79]=[CH:80][C:67]2=1>ClCCl.CN(C=O)C>[OH:81][C:77]1[C:68]2[CH2:69][C@@H:70]3[C:74]([CH3:76])([CH3:75])[C@:66]([CH3:65])([C:67]=2[CH:80]=[CH:79][CH:78]=1)[CH2:73][CH2:72][N:71]3[C:47]([C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:55]

Participants

8

Reactant 5

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10537505HCID 10537505, compound

Product 1

HCID 58375026HCID 58375026, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (155 mg; alternatively, N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate may be used) is added to a solution of benzoic acid (60 mg) and ethyldiisopropylamine (0.25 mL) in dichloromethane (1 mL; DMF may be used as well). The resulting solution is stirred at ambient temperature for 15 min before it is cooled in an ice bath. (2R,6S)-6,11,11-Trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-10-ol (0.10 g) is added and the solution is warmed to room temperature and stirred overnight. The mixture is concentrated under reduced pressure and the residue is purified by HPLC on reversed phase (H2O/MeCN) to give the product as a beige solid.

Workup

  1. temperatureis cooled in an ice bath
  2. temperaturethe solution is warmed to room temperature
  3. stirringstirred overnight
  4. concentrationThe mixture is concentrated under reduced pressure
  5. customthe residue is purified by HPLC on reversed phase (H2O/MeCN)

Sources & evidence

ORD record
ord-3e1958bf08f14bee84cda184f020688b
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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