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

HRID 2170103노트

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HRID 2170103 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8f786711be854190a216f0b30a15cfbd
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050339B2

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