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

HRID 660427
Notes
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Reaction equation

HRID 660427 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-65f8154c8fe84f59983317319f174b5d
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084497B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes