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Tetrahydrofuran → (S)-ethyl 1-((S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidine-3-carboxylate

HRID 1948477
ノート
印刷プレビュー

反応式

HRID 1948477 の反応式
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16](F)=[O:17])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH2:28]([O:30][C:31]([C@H:33]1[CH2:38][CH2:37][CH2:36][N:35]([CH2:39][C@@H:40]([OH:51])[C:41]2[CH:46]=[CH:45][C:44](/[C:47](=[N:49]/O)/[NH2:48])=[CH:43][CH:42]=2)[CH2:34]1)=[O:32])[CH3:29].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C(#N)C>[OH:51][C@@H:40]([C:41]1[CH:46]=[CH:45][C:44]([C:47]2[N:49]=[C:16]([C:10]3[O:9][N:8]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:11]=3[C:12]([F:15])([F:14])[F:13])[O:17][N:48]=2)=[CH:43][CH:42]=1)[CH2:39][N:35]1[CH2:36][CH2:37][CH2:38][C@H:33]([C:31]([O:30][CH2:28][CH3:29])=[O:32])[CH2:34]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 58374067HCID 58374067、化合物HCID 58374160HCID 58374160、化合物

生成物 1

HCID 58374192(S)-ethyl 1-((S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

3-Phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride, Int-I-G (214 mg, 0.78 mmol) was dissolved in acetonitrile (5.00 mL). DIEA (0.272 mL, 1.555 mmol) and (S)-ethyl-1-((S)-2-hydroxy-2-(4-((Z)-N′-hydroxycarbamimidoyl) phenyl)ethyl)-piperidine-3-carboxylate (261 mg, 0.778 mmol) were added. The reaction mixture was stirred for 2 hours, then 1M TBAF in THF (0.778 mL, 0.778 mmol) was added. The reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered and purified by HPLC in three batches. HPLC conditions: PHENOMENEX® Luna C18 5 micron column (250×30mm); 25-100% CH3CN/water (0.1% TFA); 25 minute gradient; 30 mL/min. Isolated fractions with correct mass were partitioned between EtOAc and saturated NaHCO3 with back extracting aqueous layer once. The organic layer was dried with MgSO4, filtered, and concentrated to give 155mg of (S)-ethyl 1-((S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidine-3-carboxylate. 1H NMR (400 MHz, MeOH-d3) δ ppm 8.04 (2H, d, J=8.13 Hz), 7.55-7.60 (2H, m), 7.41-7.54 (5H, m), 4.81 (1H, ddd, J=8.35, 4.06, 3.84 Hz), 3.96-4.10 (2H, m), 2.82-3.08 (1H, m), 2.67-2.82 (1H, m, 2.36-2.61 (3H, m), 2.08-2.33 (2H, m), 1.73-1.87 (1H, m, J=8.54, 8.54, 4.45, 4.17 Hz), 1.32-1.70 (3H, m), 1.09-1.19 (3H, m). MS (m+1)=557. HPLC Peak RT=3.36 minutes. Purity=99%.

後処理

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. filtrationThe reaction mixture was filtered
  3. custompurified by HPLC in three batches
  4. custom25 minute
  5. customIsolated fractions with correct mass were partitioned between EtOAc and saturated NaHCO3 with back extracting aqueous layer once
  6. dry with materialThe organic layer was dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-2a519b81a04145c58536443f68265e74
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08399451B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート