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

HRID 660427
ノート
印刷プレビュー

反応式

HRID 660427 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 3939Lithium Hydroxide2 回HCID 88785Acetobromo-alpha-D-glucuronic acid methyl esterHCID 9813414Faxeladol

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 962
Water
溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-65f8154c8fe84f59983317319f174b5d
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08084497B2

反応ノート

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