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Lithium Hydroxide → 6-[(1r,2r)-3-(2-Dimethylaminomethyl-cyclohexyl)-phenoxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

HRID 660427
노트
인쇄 미리보기

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HRID 660427 반응식
[CH3:1][N:2]([CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[CH3:3].CC([O:21][C@@H:22]1[C@@H:27]([O:28]C(C)=O)[C@@H:26](Br)[O:25][C@H:24]([C:33]([O:35]C)=[O:34])[C@H:23]1[O:37]C(C)=O)=O.[OH-].[Li+]>CO.O>[CH3:3][N:2]([CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][CH:26]1[O:25][CH:24]([C:33]([OH:35])=[O:34])[CH:23]([OH:37])[CH:22]([OH:21])[CH:27]1[OH:28])[CH3:1]
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참가 물질

6

반응물 3

HCID 3939Lithium Hydroxide2회HCID 88785Acetobromo-alpha-D-glucuronic acid methyl esterHCID 9813414Faxeladol

생성물 1

HCID 100929256-[(1r,2r)-3-(2-Dimethylaminomethyl-cyclohexyl)-phenoxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

시약·촉매·용매 2

HCID 887Methanol용매
HCID 962
Water
용매

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온도
20 °C

실험 절차

A mixture of 2.33 g (10 mmol) (1R,2R)-3-(2-dimethylaminomethyl-cyclohexyl)-phenol, 3.58 g (9 mmol) acetobromo-α-D-glucuronic acid methyl ester and 0.23 g (9.5 mmol) lithium hydroxide in 23 ml dry methanol was first stirred at 20° C. for 30 minutes, a solution of 0.65 g lithium hydroxide in 25 ml water was then added and the mixture was stirred again for 30 minutes. It was extracted with ethyl acetate and the aqueous phase was adjusted to a pH of 3.5 by addition of acetic acid and extracted again with ethyl acetate. The aqueous phase was evaporated in vacuo and the residue was purified by HPLC. 0.85 g (23% of theory) of the title compound was obtained in this manner in the form of a white powder.

후처리

  1. stirringthe mixture was stirred again for 30 minutes
  2. extractionIt was extracted with ethyl acetate
  3. additionthe aqueous phase was adjusted to a pH of 3.5 by addition of acetic acid
  4. extractionextracted again with ethyl acetate
  5. customThe aqueous phase was evaporated in vacuo
  6. customthe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-65f8154c8fe84f59983317319f174b5d
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084497B2

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