Triethylamine → HCID 67448480, compound

HRID 1406373Notes

Reaction equation

HRID 1406373 reaction equation
C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(OC([NH:37][C:38]1([C:41]([OH:43])=O)[CH2:40][CH2:39]1)=O)(C)(C)C.[CH3:44][O:45][C:46]1[CH:60]=[CH:59][C:49]([O:50][C:51]2[CH:58]=[CH:57][C:54]([CH2:55][NH2:56])=[CH:53][CH:52]=2)=[C:48]([C:61]([F:64])([F:63])[F:62])[CH:47]=1>CN(C=O)C>[CH3:44][O:45][C:46]1[CH:60]=[CH:59][C:49]([O:50][C:51]2[CH:58]=[CH:57][C:54]([CH2:55][NH:56][C:41]([C:38]3([NH2:37])[CH2:39][CH2:40]3)=[O:43])=[CH:53][CH:52]=2)=[C:48]([C:61]([F:62])([F:63])[F:64])[CH:47]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58487879HCID 58487879, compound

Product 1

HCID 67448480HCID 67448480, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

540 μL (3.85 mmol) of triethylamine and 864 mg (2.69 mmol) of TBTU were added to a solution of 541.5 mg (2.69 mmol) of 1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid in 45 mL DMF and the mixture was stirred for 5 min at RT. Then 800 mg (2.69 mmol) of 4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylamine (from 84a) was added and the mixture was stirred for 2 h at ambient temperature. The reaction mixture was filtered through Alox B, washed with DMF/MeOH=9/1 and the filtrate was evaporated down. 20 ml dichloromethane/trifluoroacetic acid/water=50/45/5 were added to the residue and the mixture was stirred for 1 h at RT. The reaction mixture was evaporated down, the residue was dissolved in dichloromethane and extracted with 10 mL of 1 M sodium hydroxide solution. The dichloromethane phase was separated off and evaporated down.

Workup

  1. stirringthe mixture was stirred for 2 h at ambient temperature
  2. filtrationThe reaction mixture was filtered through Alox B
  3. washwashed with DMF/MeOH=9/1
  4. customthe filtrate was evaporated down
  5. addition20 ml dichloromethane/trifluoroacetic acid/water=50/45/5 were added to the residue
  6. stirringthe mixture was stirred for 1 h at RT
  7. customThe reaction mixture was evaporated down
  8. dissolutionthe residue was dissolved in dichloromethane
  9. extractionextracted with 10 mL of 1 M sodium hydroxide solution
  10. customThe dichloromethane phase was separated off
  11. customevaporated down

Sources & evidence

ORD record
ord-f711b4edf629448ea3e2c49bef609e92
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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