Trifluoroacetic acid → HCID 10597307, compound

HRID 366215Notes

Reaction equation

HRID 366215 reaction equation
C(OC(=O)NC(C)(C)C/C=C/[C:12](=O)[N:13](C)[C@@H:14]([C:26](=[O:41])[N:27]([CH3:40])[C@@H:28]([C:36](=[O:39])[NH:37][CH3:38])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:40][N:27]([C@@H:28]([C:36](=[O:39])[NH:37][CH3:38])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:26](=[O:41])[C@H:14]([NH:13][CH3:12])[CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 10532035HCID 10532035, compound

Product 1

HCID 10597307HCID 10597307, compoundYield 130.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

((3E)-1,1-Dimethyl4-(N-methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(1-naphthyl)-ethyl)carbamoyl)but-3-enyl)carbamic acid tert butylester (0.25 g; 0.40 mmol) was dissolved in methylene chloride (3 mL) and trifluoroacetic acid (2 mL) was added. The reaction mixture was stirred for 5 min at room temperature. Methylene chloride (5 mL) and solid sodium hydrogen carbonate were added until pH 8. The reaction mixture was washed with methylene chloride (3×10 mL). The combined organic phases were dried (magnesium sulfate) and evaporated in vacuo to afford 0.21 g of the title compound.

Workup

  1. washThe reaction mixture was washed with methylene chloride (3×10 mL)
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-de27127f168a478990abfdcc6fe4ee53
Source dataset
uspto-grants-2000_10
Patent number
US06127391

Reaction notes

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