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 446563ノート

反応式

HRID 446563 の反応式
[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]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 962Water2 回HCID 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

生成物 2

HCID 517165Ammonium Acetate収率 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 acid収率 61.9%

試薬・触媒・溶媒 2

HCID 887Methanol触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0f387122be1c4ffd93f5362548f9eb74
出典データセット
uspto-grants-2013_07
特許番号
US08476253B2

反応ノート

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