Trimethyl orthoformate → HCID 66941323, compound

HRID 1173960Notes

Reaction equation

HRID 1173960 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:25][C:26](=[O:33])[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][NH2:32])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OC)(OC)OC.[BH4-].[Na+]>CO>[CH2:18]([O:25][C:26](=[O:33])[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])=[CH:10][CH:11]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 2783677Benzyl N-(4-aminobutyl)carbamateHCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateHCID 4311764Sodium borohydride

Product 1

HCID 66941323HCID 66941323, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (951.6 mg) obtained in Example 103-3 was dissolved in anhydrous methanol (38 ml) and added with (4-amino-butyl)-carbamic acid benzyl ester (898.0 mg) and trimethyl orthoformate (1.33 ml), followed by stirring at room temperature for 15.5 hours. After that, the solution was cooled with ice and added with sodium borohydride (458.5 mg), followed by stirring at room temperature for 1.5 hours. After the reaction, the solvent was distilled off and the residue was then added with water, followed by extraction with chloroform. The extract was washed with saturated saline solution and dried with anhydrous magnesium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.1479 g) as a colorless oily substance.

Workup

  1. temperatureAfter that, the solution was cooled with ice
  2. stirringby stirring at room temperature for 1.5 hours
  3. customAfter the reaction
  4. distillationthe solvent was distilled off
  5. additionthe residue was then added with water
  6. extractionfollowed by extraction with chloroform
  7. washThe extract was washed with saturated saline solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-eac6e21ddb35449491b888b2d23bd461
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

Loading…