Trifluoroacetic anhydride → HCID 58375169, compound

HRID 536689Notes

Reaction equation

HRID 536689 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[S:14]1[C:18]2[CH:19]=[C:20]([C:23]([N:25]3[CH2:32][CH2:31][C:30]4([C:34]([NH2:36])=O)[CH2:33][CH:26]3[CH2:27][C:28]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][C:29]=34)=[O:24])[CH:21]=[CH:22][C:17]=2[N:16]=[CH:15]1.C(N(C(C)C)C(C)C)C>ClCCl>[S:14]1[C:18]2[CH:19]=[C:20]([C:23]([N:25]3[CH2:32][CH2:31][C:30]4([C:34]#[N:36])[CH2:33][CH:26]3[CH2:27][C:28]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][C:29]=34)=[O:24])[CH:21]=[CH:22][C:17]=2[N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 58374955HCID 58374955, compound

Product 1

HCID 58375169HCID 58375169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (43 μL) is added to a solution of 3-(benzothiazole-6-carbonyl)-8-hydroxy-2,3,4,5-tetrahydro-1H-2,6-methano-benzo[d]azocine-6-carboxylic acid amide (40 mg) and ethyldiisopropylamine (50 μL) in dichloromethane (0.5 mL) chilled in an ice bath. The ice bath is removed and the solution is stirred at ambient temperature for 4 h. Then, another portion of trifluoroacetic anhydride (43 μL) and ethyldiisopropylamine (50 μL) are added and the solution is stirred overnight. Methanol (1 mL) is added and the solution is stirred for another 10 min. The solution is concentrated under reduced pressure and the residue is purified by HPLC on reversed phase (water/MeCN) to give the title compound.

Workup

  1. temperaturechilled in an ice bath
  2. customThe ice bath is removed
  3. additionThen, another portion of trifluoroacetic anhydride (43 μL) and ethyldiisopropylamine (50 μL) are added
  4. stirringthe solution is stirred overnight
  5. additionMethanol (1 mL) is added
  6. stirringthe solution is stirred for another 10 min
  7. concentrationThe solution is concentrated under reduced pressure
  8. customthe residue is purified by HPLC on reversed phase (water/MeCN)

Sources & evidence

ORD record
ord-aa87d82383b64fa0996550684c8f625b
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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