Acetic Acid → HCID 117629103, compound

HRID 61966Notes

Reaction equation

HRID 61966 reaction equation
[OH:1][C@@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([CH3:9])[O:4][C@H:3]1[O:10][C@H:11]([CH3:34])[CH2:12][CH2:13][C:14]([O:16][C@H:17]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:18][NH:19][C:20](=[O:27])[CH2:21][CH2:22][C:23]([O:25]C)=[O:24])=[O:15].[Li+].[OH-].O.C(O)(=O)C>O1CCCC1.O1CCOCC1>[OH:1][C@@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([CH3:9])[O:4][C@H:3]1[O:10][C@H:11]([CH3:34])[CH2:12][CH2:13][C:14]([O:16][C@H:17]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:18][NH:19][C:20](=[O:27])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 117629061HCID 117629061, compound

Product 1

HCID 117629103HCID 117629103, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To prepare pasc#9, a solution of 18 (6.6 mg, 14 μmol) in dry tetrahydrofuran (200 μl) was treated with a mixture of LiOH (0.3 mg, 12 μmol) and water (80 μl) in 1,4-dioxane (400 μl). After stirring at 60° C. for 5 minutes, the solution was acidified with glacial acetic acid and concentrated in vacuo. HPLC purification (see Methods) of the crude reaction mixture afforded 4-(((R)-2-(((R)-4-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)pentanoyl)oxy)-2-phenylethyl)amino)-4-oxobutanoic acid (pasc#9) (1.8 mg, 4 μmol, 29%) as a colorless oil.

Workup

  1. customTo prepare pasc#9
  2. concentrationconcentrated in vacuo
  3. customHPLC purification (see Methods) of the crude
  4. customreaction mixture

Sources & evidence

ORD record
ord-e4b6b755a41d44a8bebee17bc21f318c
Source dataset
uspto-grants-2016_09
Patent number
US09445596B2

Reaction notes

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