(S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate) → (S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate

HRID 453706ノート

反応式

HRID 453706 の反応式
C([C@@H]([O-])[C@@H](C(O)=O)[O-])(O)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C@@H:19]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])=[CH:14][CH:13]=1>CCOC(C)=O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C@@H:19]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])=[CH:14][CH:13]=1

参加物

3

反応物 1

HCID 86660298(S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate)

生成物 1

HCID 58556882(S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate収率 48.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

(S)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate) (diastereomer 2 of 18) (150 mg, 0.35 mmol) was dissolved in EtOAc (50 ml) and washed with a satured Na2CO3 solution (25 ml). The organic phase was dried over Na2SO4, and the solvent was removed in vacuo giving (S)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (60.0 mg, 0.17 mmol). This compound was dissolved in acetonitrile (2.5 ml), and 2-bromo-1-(4-hydroxyphenyl)-ethanone (36.0 mg, 0.17 mmol) was added. The reaction mixture was stirred at r.t. for 24 hours. The solvent was removed under vacuum and crude was purified by preparative HPLC to afford (R)-3-((S)-2-(4-fluorophenylamino)-2-phenylacetoxy)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane 2,2,2-trifluoroacetate (23.5 mg, 23% yield).

後処理

  1. washwashed with a satured Na2CO3 solution (25 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-c6ca8e8de3cd47c89e6654e0dbd2c22a
出典データセット
uspto-grants-2013_07
特許番号
US08492548B2

反応ノート

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