Formic Acid → HCID 58375229, compound

HRID 536686Notes

Reaction equation

HRID 536686 reaction equation
C(N(CC)CC)C.C(O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:30]1[C:34]2[CH:35]=[C:36]([C:39]([N:41]3[CH2:48][CH2:47][C:46]4([CH3:50])[CH2:49][CH:42]3[CH2:43][C:44]3[CH:54]=[CH:53][C:52](OS(C(F)(F)F)(=O)=O)=[CH:51][C:45]=34)=[O:40])[CH:37]=[CH:38][C:33]=2[N:32]=[CH:31]1>CN(C)C=O.[Cl-].[Na+].O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[S:30]1[C:34]2[CH:35]=[C:36]([C:39]([N:41]3[CH2:48][CH2:47][C:46]4([CH3:50])[CH2:49][CH:42]3[CH2:43][C:44]3[CH:54]=[CH:53][CH:52]=[CH:51][C:45]=34)=[O:40])[CH:37]=[CH:38][C:33]=2[N:32]=[CH:31]1

Participants

8

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 58375185HCID 58375185, compound

Product 1

HCID 58375229HCID 58375229, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

Palladiumdiacetate (10 mg), triethylamine (0.25 mL), formic acid (93 μL), and triphenylphosphine (16 mg) are added in turn to a solution of trifluoro-methanesulfonic acid 3-(benzothiazole-6-carbonyl)-6-methyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl ester (0.30 g) in dimethylformamide (1 mL) under argon atmosphere. The resulting mixture is stirred at 60° C. for 20 h. After cooling to room temperature, brine is added and the resulting mixture is extracted three times with ethyl acetate. The combined organic extracts are washed with brine and dried (Na2SO4). The solvent is evaporated under reduced pressure and the residue is purified by HPLC on reversed phase (H2O/MeCN).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe resulting mixture is extracted three times with ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is evaporated under reduced pressure
  6. customthe residue is purified by HPLC on reversed phase (H2O/MeCN)

Sources & evidence

ORD record
ord-c4ae592a8af54c7eb01e9587879733b6
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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