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Lithium Hydroxide → (R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid

HRID 77333
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인쇄 미리보기

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HRID 77333 반응식
C([O:3][C:4]([CH:6]1[C@H:13]2[CH2:14][CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]2)[N:7]1[S:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)(=[O:17])=[O:16])=[O:5])C.[OH-].[Li+]>O1CCCC1.O>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[S:15]([N:7]1[CH:6]([C:4]([OH:5])=[O:3])[C@H:13]2[CH2:14][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]2)(=[O:17])=[O:16]
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5

반응물 2

HCID 3939Lithium HydroxideHCID 67155158(R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid ethyl ester

생성물 1

HCID 67155306(R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid수율 98%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To a solution of (R)-7-(naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid ethyl ester (0.55 g, 1.42 mmol) in tetrahydrofuran (15 mL) is added a solution of lithium hydroxide (1.2 g, 28.6 mmol) in water (15 mL). The reaction is heated to 80° C. for 16 h, and the solvent is removed in vacuo. The residue is dissolved in water and washed with diethyl ether. The aqueous layer is then acidified with 6 N hydrochloric acid to pH less than 4 and extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried over magnesium sulfate, and concentrated to afford the title compound as a yellow solid (0.50 g, 98% yield). LCMS (m/z): 360.07 (M+1), 358.12 (M−1).

후처리

  1. customthe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in water
  3. washwashed with diethyl ether
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7661e73c103b45fabeba0b561fa5084b
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841291B2

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