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

HRID 923398

反応式

HRID 923398 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-af592f40ecca472c9bb07c6e1b03dfa4
出典データセット
uspto-grants-2016_03
特許番号
US09278922B2

関連ノート

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