Lithium hydroxide, monohydrate → (1R,4S)-4-[(tert-butoxycarbonyl)amino]-1-(ethoxymethyl)cyclopent-2-ene-1-carboxylic acid

HRID 270608노트

반응식

HRID 270608 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([CH2:18][O:19][CH2:20][CH3:21])([C:14]([O:16]C)=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.CO.O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([CH2:18][O:19][CH2:20][CH3:21])([C:14]([OH:16])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 57938729Methyl(1R,4S)-4-[(tert-Butoxycarbonyl)amino]-1-(ethoxymethyl)cyclopent-2-ene-1-carboxylate

생성물 1

HCID 57938736(1R,4S)-4-[(tert-butoxycarbonyl)amino]-1-(ethoxymethyl)cyclopent-2-ene-1-carboxylic acid

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl (1R,4S)-4-[(tert-butoxycarbonyl)amino]-1-(ethoxymethyl)cyclopent-2-ene-1-carboxylate (3.25 g, 10.8 mmol) in tetrahydrofuran (58.7 mL), methanol (58.7 mL) and water (12.6 mL) was added lithium hydroxide monohydrate (0.731 g, 17.42 mmol). The pink mixture was heated to reflux overnight. The organic solvents were removed in vacuo and the aqueous layer was washed once with ether and then acidified slowly with concentrated HCl until the pH reached 4. The resulting suspension was extracted with methylene chloride three times. The combined organic layers were dried over MgSO4, filtered and concentrated to give the desired product as a mixture of two cis/trans isomers (2.75 g, 89%). MS calculated for C14H24NO5: (M+H) 286.2; found 186.2 (M+H-Boc).

후처리

  1. temperatureThe pink mixture was heated
  2. temperatureto reflux overnight
  3. customThe organic solvents were removed in vacuo
  4. washthe aqueous layer was washed once with ether
  5. extractionThe resulting suspension was extracted with methylene chloride three times
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bf60838c75c044aaae32f1f8d7b27dd5
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449467B2

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