Diisopropylethylamine → [4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(3-methanesulfonyl-phenyl)-methanone acetate

HRID 1070912ノート

反応式

HRID 1070912 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:8][CH2:7]1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[CH3:46][S:47]([C:50]1[CH:51]=[C:52]([CH:56]=[CH:57][CH:58]=1)[C:53]([OH:55])=[O:54])(=[O:49])=[O:48].C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[C:53]([OH:55])(=[O:54])[CH3:52].[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH:12]2[CH2:13][CH2:14][N:15]([C:53]([C:52]3[CH:56]=[CH:57][CH:58]=[C:50]([S:47]([CH3:46])(=[O:49])=[O:48])[CH:51]=3)=[O:54])[CH2:16][CH2:17]2)[CH2:10][CH2:11]1

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 2203803-Methanesulfonylbenzoic acidHCID 516892Sodium BicarbonateHCID 2733179PyBroPHCID 223974344-(3,4-Dichloro-phenoxy)-[1,4']bipiperidine

生成物 1

HCID 22397435[4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(3-methanesulfonyl-phenyl)-methanone acetate収率 73.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The product of Step b (0.15 g) was dissolved in THF (4 ml), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PYBROP™; 0.235 g), 3-methylsulphonylbenzoic acid (0.091 g) and N,N-di-iso-propylethylamine (0.238 ml) were added. After 18 hours at room temperature ethyl acetate and aqueous NaHCO3 solution were added. The product was extracted with ethyl acetate, the combined organic extracts dried with Na2SO4 and concentrated. Purification by reverse phase HPLC (with a gradient eluent system (45% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)) gave the title compound (0.095 g).

後処理

  1. extractionThe product was extracted with ethyl acetate
  2. dry with materialthe combined organic extracts dried with Na2SO4
  3. concentrationconcentrated
  4. customPurification by reverse phase HPLC (with a gradient eluent system (45% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%))

出典と根拠

ORDレコード
ord-ec0e033ccd794f42b6a409316c8e8d32
出典データセット
uspto-grants-2005_06
特許番号
US06903115B2

反応ノート

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