Hydrochloric Acid → HCID 60143147, compound

HRID 1746823Notes

Reaction equation

HRID 1746823 reaction equation
[OH:1][C@@H:2]1[CH2:17][C@@H:5]2[S:6][C@@H:7]([CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[CH2:8][CH2:9][C@@H:4]2[C@H:3]1/[CH:18]=[CH:19]/[C@@H:20]([OH:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+].Cl>CO>[OH:1][C@@H:2]1[CH2:17][C@@H:5]2[S:6][C@@H:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:8][CH2:9][C@@H:4]2[C@H:3]1/[CH:18]=[CH:19]/[C@@H:20]([OH:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57521313HCID 57521313, compound

Product 1

HCID 60143147HCID 60143147, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound 14 (6.9 mg) was dissolved in methanol (0.4 mL), a 2M aqueous sodium hydroxide solution (0.1 mL) was added at room temperature, and the mixture was stirred overnight. Dilute hydrochloric acid was added to the reaction liquid, and the mixture was then extracted with ethyl acetate two times. The organic layers were combined, washed with a saturated saline, and dried with anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (dichloromethane: methanol=100:1→10:1) to obtain a titled compound (4.8 mg) having the following physical property values.

Workup

  1. extractionthe mixture was then extracted with ethyl acetate two times
  2. washwashed with a saturated saline
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe residue obtained by concentration under reduced pressure
  5. customwas purified by silica gel column chromatography (dichloromethane: methanol=100:1→10:1)

Sources & evidence

ORD record
ord-7e31c1e04b9c45c2a09438ed1d1d4a89
Source dataset
uspto-grants-2015_10
Patent number
US09150537B2

Reaction notes

Loading…