Trifluoroacetic anhydride → 5-(3,5-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-naphthalen-1-yl]-5-trifluoromethyl-4,5-dihydro-isoxazole

HRID 388371ノート

反応式

HRID 388371 の反応式
FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OC([N:21]1[CH:25]=[C:24]([C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([C:36]3[CH2:40][C:39]([C:45]4[CH:50]=[C:49]([Cl:51])[CH:48]=[C:47]([Cl:52])[CH:46]=4)([C:41]([F:44])([F:43])[F:42])[O:38][N:37]=3)=[CH:28][CH:27]=2)[CH:23]=[N:22]1)=O)(C)(C)C.[OH-].[Na+]>ClCCl>[Cl:51][C:49]1[CH:50]=[C:45]([C:39]2([C:41]([F:43])([F:42])[F:44])[O:38][N:37]=[C:36]([C:29]3[C:30]4[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:26]([C:24]4[CH:23]=[N:22][NH:21][CH:25]=4)=[CH:27][CH:28]=3)[CH2:40]2)[CH:46]=[C:47]([Cl:52])[CH:48]=1

参加物

5

反応物 3

HCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 674362084-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-pyrazole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 468423985-(3,5-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-naphthalen-1-yl]-5-trifluoromethyl-4,5-dihydro-isoxazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid anhydride (0.18 ml) is added to a solution of 4-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-pyrazole-1-carboxylic acid tert-butyl ester (135 mg) in dichloromethane (1 ml). After 1 hour at room temperature an aqueous solution of sodium hydroxide (30%) is added. The aqueous phase is extracted with dichloromethane and the combined organic phases are dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-(3,5-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-naphthalen-1-yl]-5-trifluoromethyl-4,5-dihydro-isoxazole as a colorless solid: m.p. 117-120° C. (compound 1.17, table 1).

後処理

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. dry with materialthe combined organic phases are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product is purified on a semi-preparative HPLC

出典と根拠

ORDレコード
ord-52533b5a58f746f1b3004fb65bc8ec0d
出典データセット
uspto-grants-2013_02
特許番号
US08377942B2

反応ノート

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