Hydrochloric Acid → (alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid

HRID 716528

반응식

HRID 716528 반응식
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[CH3:17][O:18][C:19](Cl)=[O:20].Cl>O1CCCC1.O>[CH3:17][O:18][C:19]([NH:11][C@H:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:8]([OH:10])=[O:9])=[O:20]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 70134Phenylglycine, D-HCID 516892Sodium Bicarbonate

생성물 1

HCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

D-(−)-α-Phenylglycine (0.165 mmol) was dissolved in tetrahydrofuran (500 mL), followed by the addition of NaHCO3 (0.496 mmol) in water (500 mL), and then the addition of methylchloroformate (0.182 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. The mixture was acidified to pH=3 with HCl (1N) and the volatile was concentrated in vacuo. The aqueous layer was extracted with ethyl acetate and the organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give compound 31 as a pale yellow solid in 80% yield. MS (ESI, EI+) m/z=209 (MH+).

후처리

  1. concentrationthe volatile was concentrated in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d29ace45e3554fff8245c4da1b951547
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187496B2

연결된 노트

불러오는 중…