Triethylamine → Methyl 4-{2-[(benzofuran-2-yl-carbonyl)amino]ethylsulfanyl}benzoate

HRID 29718

反応式

HRID 29718 の反応式
Cl.[NH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25](O)=[O:26].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25]([NH:2][CH2:3][CH2:4][S:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)=[O:26]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 10331Benzofuran-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66687893Methyl 4-(2-aminoethylsulfanyl)benzoate hydrochloride

生成物 1

HCID 66687946Methyl 4-{2-[(benzofuran-2-yl-carbonyl)amino]ethylsulfanyl}benzoate収率 38.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Methyl 4-(2-aminoethylsulfanyl)benzoate hydrochloride (0.248 g, 1.00 mmol), was combined with benzofuran-2-carboxylic acid (0.162 g, 1.00 mmol) and HBTU (0.379 g, 1.00 mmol) in DMF (5 ml) at room temperature. Triethylamine (0.307 ml, 2.2 mmol) was added and the reaction mixture was stirred at room temperature overnight. Saturated aqueous NaHCO3 (15 ml) was added to give precipitates which was broken up by the addition of water (20 ml). The solid was filtered and the cake was dissolved in ethyl acetate. The residual water was removed by pipette and hexane was added to give methyl 4-{2-[(benzofuran-2-yl-carbonyl)-amino]ethylsulfanyl}benzoate (0.138 g) as a gum which was used in the next step without further purification.

後処理

  1. customto give
  2. customprecipitates which
  3. additionwas broken up by the addition of water (20 ml)
  4. filtrationThe solid was filtered
  5. dissolutionthe cake was dissolved in ethyl acetate
  6. customThe residual water was removed by pipette and hexane
  7. additionwas added

出典と根拠

ORDレコード
ord-14f61712884949cfaf2783c6c5b1ae07
出典データセット
uspto-grants-2008_09
特許番号
US07420089B2

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