Trifluoroacetic acid → (S)-2-Amino-3-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-yl]-propionic acid methyl ester

HRID 76798Notes

Reaction equation

HRID 76798 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][C@H:13]3[C:18]([O:19][CH3:20])=N[C@H](C(C)C)C(OC)=[N:14]3)[CH:8]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=[O:27].C([O-])(O)=O.[Na+]>C(#N)C>[CH3:20][O:19][C:18](=[O:27])[C@@H:13]([NH2:14])[CH2:12][C:9]1[CH:8]=[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[O:11][N:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66911151(2S,5R)-2-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine

Product 1

HCID 66911101(S)-2-Amino-3-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-yl]-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Intermediate 1 (3.25 g, 8.51 mmol) in acetonitrile (183 ml) was treated with TFA (90 ml, 2 M in water) and stirred at RT overnight. After complete conversion the mixture was neutralized with sat. aq. NaHCO3-solution, the majority of the acetonitrile was evaporated and the remainder extracted with ethyl acetate. The combined organic phases were washed with brine, dried with MgSO4, filtered and evaporated to dryness. The resulting crude oil (2.5 g) was used in the next steps without further purification.

Workup

  1. customthe majority of the acetonitrile was evaporated
  2. extractionthe remainder extracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting crude oil (2.5 g) was used in the next steps without further purification

Sources & evidence

ORD record
ord-3bd6eae54ada439589fee5134814a623
Source dataset
uspto-grants-2014_09
Patent number
US08835653B2

Reaction notes

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