Methanol → 3-(Benzothiazol-6-ylamino)-butyric acid

HRID 2383967

반응식

HRID 2383967 반응식
C([O:3][C:4](=[O:9])[CH2:5][CH:6]([NH2:8])[CH3:7])C.I[C:11]1[CH:19]=[CH:18][C:14]2[N:15]=[CH:16][S:17][C:13]=2[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CO>CN(C=O)C.C(Cl)(Cl)Cl.[Cu](I)I>[S:17]1[C:13]2[CH:12]=[C:11]([NH:8][CH:6]([CH3:7])[CH2:5][C:4]([OH:3])=[O:9])[CH:19]=[CH:18][C:14]=2[N:15]=[CH:16]1

참가 물질

8

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 98103Ethyl 3-aminobutyrateHCID 226090026-Iodo-1,3-benzothiazole

생성물 1

HCID 596361913-(Benzothiazol-6-ylamino)-butyric acid수율 22.22%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

3-Amino-butyric acid ethyl ester (2 g, 15.27 mmol), 6-iodo-benzothiazole (3.98 g, 15.27 mmol) and potassium carbonate (5.27 g, 38.18 mmol) were dissolved in DMF (50 mL) and the reaction mixture was purged with argon for 10 minutes. This was followed by the addition of copper iodide (290 mg, 1.527 mmol) and the resulting mixture was heated to 110° C. overnight. The reaction was monitored by TLC (10% MeOH in CHCl3) which showed the presence of starting material. The reaction mixture was heated to 120° C. for a further 24 hours. The reaction mixture was concentrated and adjusted the pH to 5 using acetic acid. The reaction mixture was partitioned between water and ethylacetate. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 800 mg of the product (22.22% yield).

후처리

  1. customthe reaction mixture was purged with argon for 10 minutes
  2. temperatureThe reaction mixture was heated to 120° C. for a further 24 hours
  3. concentrationThe reaction mixture was concentrated
  4. customThe reaction mixture was partitioned between water and ethylacetate
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-adee0a0707474db8b57c5e0c4131c329
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263635B2

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