Methanol → HCID 10896843, 화합물

HRID 525329

반응식

HRID 525329 반응식
S(Cl)(Cl)=O.[CH:5]1[C:10]([C@H:11]([NH2:15])[C:12]([OH:14])=[O:13])=[CH:9][CH:8]=[C:7]([F:16])[CH:6]=1.[CH3:17]O>CCOC(C)=O>[NH2:15][C@@H:11]([C:10]1[CH:9]=[CH:8][C:7]([F:16])=[CH:6][CH:5]=1)[C:12]([O:14][CH3:17])=[O:13]

참가 물질

5

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 853015(S)-4-Fluorophenylglycine

생성물 1

HCID 10896843HCID 10896843, 화합물수율 100%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Thionyl chloride (0.475 mL, 6.50 mmol) was added dropwise to a solution of (S)-4-fluorophenylglycine (commercially available from Sigma-Aldrich, Milwaukee, Wis.)(1.00 g, 5.91 mmol) in MeOH (25.0 mL), and the mixture was stirred at reflux for 2 hours. The reaction mixture was then concentrated to afford a brown oil. The residue was dissolved in EtOAc, and the solution was partitioned between EtOAc and saturated aqueous NaHCO3 solution. The aqueous phase was separated and extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford (S)-methyl 2-amino-2-(4-fluorophenyl)acetate (1.1 g, 6.0 mmol, 100% yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.28 (br. s., 2H), 3.59 (s, 3H), 4.55 (s, 1H), 7.05-7.23 (m, 2H), 7.31-7.53 (m, 2H). m/z (ESI) 184 (M+H)+.

후처리

  1. temperatureat reflux for 2 hours
  2. concentrationThe reaction mixture was then concentrated
  3. customto afford a brown oil
  4. customthe solution was partitioned between EtOAc and saturated aqueous NaHCO3 solution
  5. customThe aqueous phase was separated
  6. extractionextracted with EtOAc
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ca7f0ffdd4074ea59384e6a982d2e5ca
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340549B2

연결된 노트

불러오는 중…