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

HRID 76798노트

반응식

HRID 76798 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3bd6eae54ada439589fee5134814a623
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835653B2

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