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

HRID 76798ノート

反応式

HRID 76798 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3bd6eae54ada439589fee5134814a623
出典データセット
uspto-grants-2014_09
特許番号
US08835653B2

反応ノート

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