Acetic Acid → HCID 57487078, compound

HRID 1044484Notes

Reaction equation

HRID 1044484 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][CH2:18][NH:19][S:20]([C:23]3[N:24]=[CH:25][N:26]([CH3:28])[CH:27]=3)(=[O:22])=[O:21])[CH:14]=2)[CH2:9][CH2:8][CH:7]1[NH:29][C:30](=O)OCC.[CH:39](=O)C.C(O)(=O)C.C([BH3-])#N.[Na+]>ClCCl.O.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:5][CH:6]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][NH:19][S:20]([C:23]3[N:24]=[CH:25][N:26]([CH3:28])[CH:27]=3)(=[O:22])=[O:21])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[NH:29][CH2:30][CH3:39]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 46870449Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

Product 1

HCID 57487078HCID 57487078, compoundYield 30.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (example 3, 60.0 mg, 0.103 mmol) was dissolved in dichloromethane (5 ml) and acetaldehyde (5.45 mg, 0.124 mmol μl) and molsieve 3 {acute over (Å)} were added and the mixture was stirred for 3 h. Acetic acid (7.07 mg, 0.118 mmol) was added and the mixture was stirred for another 3 h. MeOH (5 ml) and sodium cyanoborohydride (14.8 mg, 0.236 mmol) were added and it was stirred for another 14 h. Water was added and it was extracted with dichloromethane. The organic layer was washed with saturated NaHCO3 solution, washed and evaporated. The residue was purified by column chromatography using SiO2 and CH2Cl2/MeOH 95:5→90:10. The product was precipitated as an HCl salt from 6N HCl in isopropanol and isopropylether to obtain the product as a white salt (17 mg, 25%).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for another 3 h
  3. stirringit was stirred for another 14 h
  4. extractionit was extracted with dichloromethane
  5. washThe organic layer was washed with saturated NaHCO3 solution
  6. washwashed
  7. customevaporated
  8. customThe residue was purified by column chromatography
  9. customThe product was precipitated as an HCl salt from 6N HCl in isopropanol and isopropylether

Sources & evidence

ORD record
ord-16ae25cc31b0414595ebcc5d69a2766b
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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