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Lithium hydroxide, monohydrate → 6-(Benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoic acid

HRID 2177784
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HRID 2177784 반응식
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19]C)=[O:18])=[C:15]([NH:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:14]([C:32]3[CH:36]=[CH:35][O:34][CH:33]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>O.O1CCOCC1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([NH:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[C:14]([C:32]3[CH:36]=[CH:35][O:34][CH:33]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 67108007Methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoate2회

생성물 1

HCID 671077416-(Benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoic acid수율 89.4%

시약·촉매·용매 2

HCID 962Water용매2회
HCID 31275
1,4-Dioxane
용매

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온도
100 °C

실험 절차

Methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)-ethylamino]-3-(furan-3-yl)benzoate (Intermediate 122, 0.115 g) was added to a solution of lithium hydroxide monohydrate (0.168 g) in water (1 ml) and dioxane (3 ml) and the mixture was heated at 100° C. for 1 hour. The reaction was cooled to room temperature, diluted with water and washed with diethyl ether. The aqueous layer was acidified with acetic acid and extracted with ethyl acetate, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM:MeOH:AcOH:water (350:20:3:2) to give 6-(benzenesulphonylmethyl)-2-[2-(tert-butoxycarbonylamino)-ethylamino]-3-(furan-3-yl)benzoic acid (0.1 g) as a pale yellow gum.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of DCM:MeOH:AcOH:water (350:20:3:2)

출처 및 근거

ORD 기록
ord-5457a007b60b4146b84938649f56d6d3
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067905B2

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