Hydrochloric Acid → 6-[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]-5-ethyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine

HRID 132886Notes

Reaction equation

HRID 132886 reaction equation
Cl.C(OC([NH:9][C@H:10]([CH2:26][C:27]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[CH:29][C:28]=1[F:35])[CH2:11][C:12]([N:14]1[CH2:23][CH2:22][C:21]2[C:16](=[N:17][CH:18]=[CH:19][N:20]=2)[CH:15]1[CH2:24][CH3:25])=[O:13])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>CO>[NH2:9][C@H:10]([CH2:26][C:27]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[CH:29][C:28]=1[F:35])[CH2:11][C:12]([N:14]1[CH2:23][CH2:22][C:21]2[C:16](=[N:17][CH:18]=[CH:19][N:20]=2)[CH:15]1[CH2:24][CH3:25])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 691825996-[(3R)-3-(tert-Butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoyl]-5-ethyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine

Product 1

HCID 586223906-[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]-5-ethyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methanolic hydrogen chloride (approx. 1.6M, 1.5 mL) was added to 6-[(3R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoyl]-5-ethyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine (18 mg, 0.038 mmol) dissolved in 0.25 mL of methanol. After 2.5 h, the solution was added to saturated aqueous sodium bicarbonate solution (10 mL), which was then extracted with two portions of ethyl acetate (25 mL and 15 mL). The organic layers were washed in succession with saturated aqueous brine (5 mL), dried over sodium sulfate, decanted, and concentrated. The residue was dissolved in methanol, and the resulting solution was filtered (0.45 micron PTFE membrane) and evaporated to provide the title compound as a very viscous colorless syrup. LC/MS: 379 (M+1).

Workup

  1. extractionwas then extracted with two portions of ethyl acetate (25 mL and 15 mL)
  2. washThe organic layers were washed in succession with saturated aqueous brine (5 mL)
  3. dry with materialdried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in methanol
  7. filtrationthe resulting solution was filtered (0.45 micron PTFE membrane)
  8. customevaporated

Sources & evidence

ORD record
ord-39852303f0b04081b1abed26f9bb304c
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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