Acetic Acid → HCID 57487078、化合物

HRID 510502ノート

反応式

HRID 510502 の反応式
[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]

参加物

8

反応物 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

生成物 1

HCID 57487078HCID 57487078、化合物収率 30.7%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-96fb2410b76b496da16c0793b2899ef8
出典データセット
uspto-grants-2015_08
特許番号
US09096619B2

反応ノート

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