Sodium Carbonate → (R)-2-morpholino-2-phenylacetic acid

HRID 923398

반응식

HRID 923398 반응식
[NH2:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[O:15]1[CH2:16][CH2:17][N:1]([C@H:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([OH:5])=[O:4])[CH2:13][CH2:14]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 70134Phenylglycine, D-

생성물 1

HCID 1090521(R)-2-morpholino-2-phenylacetic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To (R)-2-amino-2-phenylacetic acid (1.0 g, 6.62 mmol), 1-bromo-2-(2-bromoethoxy)ethane (1.686 g, 0.727 mmol) and sodium carbonate (2.103 g, 19.85 mmol) was added ethanol (40 mL) and the resultant mixture heated at 100° C. for 45 hours. After cooling, the resultant solid was removed by filtration and washed with ethanol. The filtrate was concentrated, and then dissolved in ethanol then a solution of 4N aqueous hydrochloric acid added until the pH of the solution was 3. The resultant solid was removed and discarded. The filtrate was concentrated and purified by reversed phase chromatography (C18), eluting with 10-100% acetonitrile in water (0.1% TFA) to give the title compound. MS (ESI) m/z 222 (MA)+.

후처리

  1. temperatureAfter cooling
  2. customthe resultant solid was removed by filtration
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. dissolutiondissolved in ethanol
  6. additiona solution of 4N aqueous hydrochloric acid added until the pH of the solution
  7. customThe resultant solid was removed
  8. concentrationThe filtrate was concentrated
  9. custompurified by reversed phase chromatography (C18)
  10. washeluting with 10-100% acetonitrile in water (0.1% TFA)

출처 및 근거

ORD 기록
ord-af592f40ecca472c9bb07c6e1b03dfa4
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278922B2

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