Hydrochloric Acid → HCID 86679503、化合物

HRID 1776598ノート

反応式

HRID 1776598 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[N:13]([CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[S:14]([CH3:17])(=[O:16])=[O:15].Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N:13]([CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[S:14]([CH3:17])(=[O:16])=[O:15]

参加物

4

反応物 2

HCID 313Hydrochloric Acid2 回HCID 86679549HCID 86679549、化合物

生成物 1

HCID 86679503HCID 86679503、化合物収率 91.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of methyl 4-methoxy-3-(N-(2-morpholinoethyl)-methylsulfonamido)benzoate (0.902 g, theoric 2.314 mmol) in dioxane (23 ml), HCl 6N (4.63 ml, 27.8 mmol) was added, and the mixture was heated to 100° C. Additional HCl 6N (3.47 ml, 20.83 mmol) was added in two portion over 24 hours with stirring at the same temperature. The volatiles were removed under vacuum and the residue was dissolved in water (20 ml) and basified with NaHCO3 sat sol. (pH 7-8). The aqueous phase was washed with EtOAc and evaporated to dryness. The residue was purified by flash chromatography on silica gel column (DCM:MeOH=9:1 to 7:3) affording 4-methoxy-3-(N-(2-morpholinoethyl)methylsulfonamido)benzoic acid (0.758 g, 2.115 mmol, 91% yield over two steps, MS/ESI+ 358.9 [MH]+).

後処理

  1. customThe volatiles were removed under vacuum
  2. dissolutionthe residue was dissolved in water (20 ml)
  3. washThe aqueous phase was washed with EtOAc
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography on silica gel column (DCM:MeOH=9:1 to 7:3)

出典と根拠

ORDレコード
ord-8bbc5e832bec4d23ba2a576a04cd3731
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

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