Hydrochloric Acid → 7-[({[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]heptanoic acid

HRID 446563노트

반응식

HRID 446563 반응식
[F:1][C:2]([F:61])([F:60])[C:3]1[CH:4]=[C:5]([CH:53]=[C:54]([C:56]([F:59])([F:58])[F:57])[CH:55]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36][CH2:37][C:38]([N:40]([CH3:52])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([O:49]CC)=[O:48])=[O:39])[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7].[OH-].[Na+].O.Cl>O1CCCC1.CO>[C:47]([O-:49])(=[O:48])[CH3:46].[NH4+:8].[F:59][C:56]([F:57])([F:58])[C:54]1[CH:53]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:61])[F:60])[CH:55]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36][CH2:37][C:38]([N:40]([CH3:52])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48])=[O:39])[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 962Water2회HCID 14798Sodium HydroxideHCID 86663457Ethyl 7-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]heptanoate

생성물 2

HCID 517165Ammonium Acetate수율 0.1%HCID 866634597-[({[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]heptanoic acid수율 61.9%

시약·촉매·용매 2

HCID 887Methanol촉매HCID 8028Tetrahydrofuran용매

실험 절차

The compound (595 mg, 0.901 mmol) obtained in Example 68b was dissolved in tetrahydrofuran (12 mL), a 1 N aqueous sodium hydroxide solution (1.03 mL, 1.03 mmol), water (0.3 mL) and methanol (4 drops) were added, and the mixture was stirred at room temperature. After the reaction was completed, 1 N hydrochloric acid and water were added, the mixture was extracted with methylene chloride, and the resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by reverse phase liquid chromatography (XTerra Prep MS C18 OBD, 5 μm, 30×100 mm) (acetonitrile:0.1% aqueous ammonium acetate solution, 10:90→100:0, v/v) to give the title compound (233 mg; yield, 40%).

후처리

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialthe resulting organic layer was dried with anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by reverse phase liquid chromatography (XTerra Prep MS C18 OBD, 5 μm, 30×100 mm) (acetonitrile

출처 및 근거

ORD 기록
ord-0f387122be1c4ffd93f5362548f9eb74
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476253B2

반응 노트

불러오는 중…