Benzyl chloroformate → (3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

HRID 16388

반응식

HRID 16388 반응식
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[NH:15][C@@H:14]([C@H:16]([OH:18])[CH3:17])[CH2:13][O:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].O.C(=O)(O)[O-].[Na+].Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>O1CCCC1.O.C(OCC)(=O)C>[CH2:29]([O:28][C:26]([N:15]1[C@H:10]([C:4]2[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=2)[CH2:11][O:12][CH2:13][C@@H:14]1[C@H:16]([OH:18])[CH3:17])=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

7

반응물 3

HCID 10387Benzyl chloroformate2회HCID 67374002(R)-1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]ethanolHCID 86585896Sodium bicarbonate water

생성물 1

HCID 67373415(3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (R)-1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]ethanol (2 g) in tetrahydrofuran (20 mL) was added saturated sodium bicarbonate water (20 mL) and benzyl chloroformate (1.31 mL). After stirring the reaction solution at room temperature for 16 hours, benzyl chloroformate (1.33 mL) was further added thereto, and the mixture was then stirred for another 20 hours. The resultant solution was diluted with water and ethyl acetate. The organic layer was partitioned, washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate), to thereby obtain the titled compound (880 mg). The physical properties of this crude product were as follows.

후처리

  1. stirringthe mixture was then stirred for another 20 hours
  2. customThe organic layer was partitioned
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSolvent was removed by distillation under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-a67cc7744e6c493b8540664ed49f314e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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