Hydrochloric Acid → HCID 101575822, compound

HRID 1499971Notes

Reaction equation

HRID 1499971 reaction equation
[S:1]1[CH:5]=[CH:4][S:3][C:2]1=[C:6]1[S:10][C:9]2[S:11][C:12](=[C:14]3[S:18][C:17]([C:19]([O:21]C)=[O:20])=[CH:16][S:15]3)[S:13][C:8]=2[S:7]1.O1CCOCC1.[Li+].[OH-].Cl>CO.C1COCC1>[S:1]1[CH:5]=[CH:4][S:3][C:2]1=[C:6]1[S:7][C:8]2[S:13][C:12](=[C:14]3[S:18][C:17]([C:19]([OH:21])=[O:20])=[CH:16][S:15]3)[S:11][C:9]=2[S:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 117651040HCID 117651040, compound

Product 1

HCID 101575822HCID 101575822, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 (125 mg, 0.285 mmol) was suspended in a mixed solvent of 1,4-dioxane (50 ml), THF (50 ml), and MeOH (50 ml). The resultant mixture was charged with 2 N LiOH (28.5 ml, 57.0 mmol). The mixture was vigorously stirred for 15 hours at room temperature, then 2 N HCl (28.5 ml) was gradually added dropwise, and the mixture was adjusted to a pH of 2 to 3 by further adding 2 N HCl (2.0 ml) while checking the pH. The mixture was stirred for 20 minutes at room temperature, and then filtered using a membrane filter (H010A047A, Advantec). The filtered product was successively washed with water, methanol, and then chloroform, and dried under reduced pressure to obtain the target product Compound 1 (110 mg, 91%) as a glossy silvery-red film-like solid.

Workup

  1. stirringThe mixture was stirred for 20 minutes at room temperature
  2. filtrationfiltered
  3. filtrationfilter (H010A047A, Advantec)
  4. washThe filtered product was successively washed with water, methanol
  5. dry with materialchloroform, and dried under reduced pressure

Sources & evidence

ORD record
ord-5a64e2b3d5224ac6bb9eb704acef1dee
Source dataset
uspto-grants-2015_12
Patent number
US09202605B2

Reaction notes

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