Trifluoroacetic acid → HCID 54010737, compound

HRID 1934694Notes

Reaction equation

HRID 1934694 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][CH2:18][C@@H:17]([NH:20][C:21]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][C:22]=2[C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)=[O:24])[CH2:16]1)=O)(C)(C)C>C(Cl)(Cl)Cl>[C:41]([C:38]1[CH:39]=[CH:40][C:21]([NH:20][C@@H:17]2[CH2:18][CH2:19][NH:15][CH2:16]2)=[C:22]([CH:37]=1)[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)=[O:24])#[N:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54243370HCID 54243370, compound

Product 1

HCID 54010737HCID 54010737, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of (R)-2-[1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino]-5-cyano-N-(3,4-dimethoxybenzyl)benzamide (918 mg) in chloroform (5 mL). The mixture was stirred for 4 hours at ambient temperature and concentrated in vacuo. The residue was partitioned between chloroform and an aqueous saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give (R)-5-cyano-N-(3,4-dimethoxybenzyl)-2-(3-pyrrolidinylamino)benzamide (610 mg) as amorphous powders.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between chloroform
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d035480e6e5442318e104ac3a104d50b
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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