(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 453706노트

반응식

HRID 453706 반응식
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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-c6ca8e8de3cd47c89e6654e0dbd2c22a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492548B2

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