Hydrochloric Acid → 3-(2-Dipropylcarbamoylmethoxycarbonyl-ethylsulfamoyl)-benzoic acid

HRID 2170103ノート

反応式

HRID 2170103 の反応式
FC(F)(F)C(O)=O.[CH2:8]([N:11]([CH2:21][CH2:22][CH3:23])[C:12]([CH2:14][O:15][C:16](=[O:20])[CH2:17][CH2:18][NH2:19])=[O:13])[CH2:9][CH3:10].Cl[S:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([OH:33])=[O:32])(=[O:27])=[O:26].O.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:21]([N:11]([CH2:8][CH2:9][CH3:10])[C:12]([CH2:14][O:15][C:16]([CH2:17][CH2:18][NH:19][S:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([OH:33])=[O:32])(=[O:27])=[O:26])=[O:20])=[O:13])[CH2:22][CH3:23]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 866633463-Amino-propionic acid dipropylcarbamoylmethyl ester trifluoroacetate

生成物 1

HCID 667975393-(2-Dipropylcarbamoylmethoxycarbonyl-ethylsulfamoyl)-benzoic acid

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred solution of 3-amino-propionic acid dipropylcarbamoylmethyl ester (step 2) (20.1 g, 75 mmol) in DCM (240 ml) at 0° C. under N2 was added DMAP (0.46 g, 3.76 mmol) followed by TEA (38.8 ml, 278 mmol). The reaction mixture was treated with a solution of 3-chlorosulfonylbenzoic acid (16.6 g, 75 mmol) in DCM (200 ml). The mixture was allowed to stir at 0° C. for 1 h and then warmed up to RT for 1 h. Water (200 ml) was added and the pH adjusted with 1N HCl (100 ml). The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification by C18 reverse phase chromatography, eluting with MeCN/water (1% HCl) afforded the title product; LC-MS Rt 1.01 mins; 415.2 [M+H]+, Method 2minLC_v003.

後処理

  1. temperaturewarmed up to RT for 1 h
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by C18 reverse phase chromatography
  6. washeluting with MeCN/water (1% HCl)

出典と根拠

ORDレコード
ord-8f786711be854190a216f0b30a15cfbd
出典データセット
uspto-grants-2015_06
特許番号
US09050339B2

反応ノート

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