Hydrochloric Acid → HCID 135511908, compound

HRID 2253253Notes

Reaction equation

HRID 2253253 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[S:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:6]=2[N:7]=1.Cl.[OH-:23].[Na+]>>[NH2:1][C:2]1[NH:3][C:4](=[O:23])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[S:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58655377HCID 58655377, compound

Product 1

HCID 135511908HCID 135511908, compound

Procedure

A mixture of the compound from Step F in 2N aqueous NaOH is stirred at reflux temperature for 1.5 h. The solution is cooled in an ice-bath, neutralized with 2 N aqueous HCl and evaporated to dryness. The residue is suspended in MeOH, mixed with silica gel and evaporated. The solid residue is placed onto a silica gel column (packed in a solvent system of CH2Cl2/MeOH). The compound is eluted with a solvent system of CH2Cl2/MeOH. The fractions containing the product are collected and evaporated to dryness to yield the title compound 2-7.

Workup

  1. temperatureat reflux temperature for 1.5 h
  2. temperatureThe solution is cooled in an ice-bath
  3. customevaporated to dryness
  4. additionmixed with silica gel
  5. customevaporated
  6. washThe compound is eluted with a solvent system of CH2Cl2/MeOH
  7. additionThe fractions containing the product
  8. customare collected
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-191e96e4da4b4e5899389b4eb93f109d
Source dataset
uspto-grants-2008_01
Patent number
US07323449B2

Reaction notes

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