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Hydrochloric Acid → 3-Hydroxy-4-(3-(4-pentylphenylsulfonamido)propanamido)benzoic acid

HRID 493156
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HRID 493156 반응식
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=O)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[NH2:31])[C:25]([OH:27])=[O:26].Cl>CN(C=O)C>[OH:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[NH:31][C:18](=[O:20])[CH2:17][CH2:16][NH:15][S:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH:10]=1)(=[O:13])=[O:14])[C:25]([OH:27])=[O:26]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 1375664-Amino-3-hydroxybenzoic acidHCID 690579943-(4-Pentylphenylsulfonamido)propanoic acid

생성물 1

HCID 690603703-Hydroxy-4-(3-(4-pentylphenylsulfonamido)propanamido)benzoic acid수율 115.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
40 °C

실험 절차

To a solution of the product of Step 1 (200 mg, 0.67 mmol) in dry DMF (7 mL) was added 1,1-carbonyldiimidazole (CDI) (120 mg, 0.73 mmol). The resulting mixture was stirred at 40° C. for 1 h, then treated with 3-hydroxy-4-aminobenzoic acid (107 mg, 0.7 mmol). The mixture was stirred at 40° C. for 16 h, then poured into 1N aqueous HCl (100 mL). The resulting yellow precipitate was filtered, washed with diethyl ether, and azeotroped to dryness once from toluene to give the crude title compound (337 mg), which was used directly in the next step without further purification. MS m/e 434.

후처리

  1. stirringThe mixture was stirred at 40° C. for 16 h
  2. filtrationThe resulting yellow precipitate was filtered
  3. washwashed with diethyl ether
  4. customazeotroped to dryness once from toluene

출처 및 근거

ORD 기록
ord-16de4f4ea1b24ad0b6cfa4c873dd583d
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07534804B2

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