Trifluoroacetic acid → 3-(Benzyloxycarbonyl)amino-6-methyl-1-carboxymethyl-2-pyridinone

HRID 48888Notes

Reaction equation

HRID 48888 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:27])[N:14]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[C:15]([CH3:18])=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:27])[N:14]([CH2:19][C:20]([OH:22])=[O:21])[C:15]([CH3:18])=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10248693HCID 10248693, compound

Product 1

HCID 100186233-(Benzyloxycarbonyl)amino-6-methyl-1-carboxymethyl-2-pyridinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-benzyloxycarbonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone (6.0 g, 17 mmol), as prepared in step 2 of Example 1, in methylene chloride (12 mL) was added trifluoroacetic acid (12 mL) and the reaction stirred at ambient temperature. After 30 minutes the reaction was concentrated in vacuo, dissolved in methylene chloride, and diluted with hexane. The precipitated product was collected by filtration and dried in vacuo giving a quantitative yield of white solid. 1H NMR (300 MHz, DMSO-d6) δ13.17 (br s, 1 H), 8.36 (s, 1H), 7.74 (d, 1H, J=7.5 Hz), 7.35 (m, 5H), 6.18 (d, 1H, J=7.7Hz), 5.15 (s, 2H), 4.77 (s, 2H), 2.25 (s, 3H).

Workup

  1. concentrationAfter 30 minutes the reaction was concentrated in vacuo
  2. dissolutiondissolved in methylene chloride
  3. additiondiluted with hexane
  4. filtrationThe precipitated product was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-abccbfd25ed141dd9755b6362f566e25
Source dataset
uspto-grants-2004_03
Patent number
US06706021B2

Reaction notes

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