Hydrochloric Acid → (R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid

HRID 885501

반응식

HRID 885501 반응식
[NH2:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=[O:4].Br[C:11]1[CH:12]=[C:13]([CH3:19])[C:14]([F:18])=[C:15]([CH3:17])[CH:16]=1.C([O-])([O-])=O.[K+].[K+].Cl>C(OCC)(=O)C.O.[Cu]I.CC(N(C)C)=O>[F:18][C:14]1[C:15]([CH3:17])=[CH:16][C:11]([NH:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=[O:4])=[CH:12][C:13]=1[CH3:19]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 456468Norleucine, D-(-)-HCID 27362985-Bromo-2-fluoro-1,3-dimethylbenzene

생성물 1

HCID 69189506(R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

반응 조건

온도
90 °C

실험 절차

(R)-2-Amino-hexanoic acid (0.840 g, 6.4 mmol), 5-bromo-2-fluoro-1,3-dimethyl-benzene (1.292 g, 6.4 mmol), CuI (0.122 g, 0.64 mmol), and K2CO3 (1.326 g, 9.6 mmol) were weighed into a Schlenk flask. To this was added 8 mL of dimethylacetamide and the resulting mixture vacuum-pumped and nitrogen-filled alternatively three times. After heating to 90° C. with stirring for 39 h, the reaction mixture was cooled to room temperature, diluted with 20 mL of ethyl acetate and 10 mL of water, and then acidified with concentrated HCl to pH=3. The layers were separated and the aqueous layer extracted with ethyl acetate (20 mL×5). The organic layers were combined and dried over anhydrous Na2SO4. Removal of the solvent under reduced pressure gave the title product which was used directly in the next step with further purification. LC-MS: tR=8.5 min, m/z 254 (M+H)+.

후처리

  1. additionthe resulting mixture vacuum-pumped and nitrogen-filled alternatively three times
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with ethyl acetate (20 mL×5)
  5. dry with materialdried over anhydrous Na2SO4
  6. customRemoval of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-fa77dd1252564d68b6b8a2dd1d36679e
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242174B2

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