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Hydrochloric Acid → 2-chloro-4-{[(3S)-1-ethyl-5-oxo-3-pyrrolidinyl]amino}benzonitrile

HRID 1160406
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HRID 1160406 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][NH:21][CH2:22][CH3:23])[CH2:12][C:13](OC(C)(C)C)=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]2[CH2:12][C:13](=[O:14])[N:21]([CH2:22][CH3:23])[CH2:20]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 595162371,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(ethylamino)butanoate

생성물 1

HCID 595161932-chloro-4-{[(3S)-1-ethyl-5-oxo-3-pyrrolidinyl]amino}benzonitrile수율 54.2%

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
65 °C

실험 절차

A solution of 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(ethylamino)butanoate (5.66 g, 16.8 mmol), HCl (4M in dioxane, 40 mL) and MeOH (100 mL) was stirred at 65° C. for 2 h. After cooling, the reaction was concentrated. To the residue, K2CO3 (325 mesh, 6.6 g, 47.5 mmol) and MeOH (150 mL) were added and the reaction was stirred at 65° C. for 1 h. Solvent was removed and the residue was partitioned between EtOAc and H2O. The organic layer was dried over MgSO4 and concentrated to give the product as a white solid (2.4 g, 54%). LC-MS (ES) m/e 264.4 (M+H)+.

후처리

  1. temperatureAfter cooling
  2. concentrationthe reaction was concentrated
  3. customSolvent was removed
  4. customthe residue was partitioned between EtOAc and H2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-64e625d5c1734adb8737ae61691b7927
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07816395B2

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