Acetic Acid → HCID 10096972, compound

HRID 1173965Notes

Reaction equation

HRID 1173965 reaction equation
N[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:25][C:26]2[NH:27][CH:28]=[CH:29][N:30]=2)[CH2:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].[C:31]([BH3-])#[N:32].[Na+].[C:35](O)(=O)[CH3:36].[CH3:39]O>>[NH:27]1[CH:28]=[CH:29][N:30]=[C:26]1[CH2:25][N:17]([CH2:16][C:13]1[CH:14]=[CH:15][C:10]([S:7]([NH:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:32][CH2:31][CH:35]([CH3:36])[CH3:39])(=[O:9])=[O:8])=[CH:11][CH:12]=1)[CH2:18][C:19]1[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 66941735HCID 66941735, compound

Product 1

HCID 10096972HCID 10096972, compound

Procedure

The compound (86.1 mg) obtained in Example 102-4 was dissolved in anhydrous methanol (3.4 ml). Then, the solution was added with isobutylaldehyde (0.055 ml) and sodium cyanoborohydride (50.3 mg) and adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 16.5 hours. After the reaction, the solvent was distilled off. Subsequently, the residue was added with a 1 mol/l sodium hydroxide aqueous solution (2.0 ml), followed by extraction with chloroform. The extract was dried with magnesium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (3.8 mg) of the subject compound as a white solid.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionSubsequently, the residue was added with a 1 mol/l sodium hydroxide aqueous solution (2.0 ml)
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe extract was dried with magnesium sulfate
  6. distillationthe solvent was then distilled off
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-4842e5a06cf64f1e9259547bf1c546cd
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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