Triethylamine → 2,6-Difluoro-3-(n-(propylsulfonyl)propyl-sulfonamido)benzoic acid

HRID 1943845노트

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HRID 1943845 반응식
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].[NH2:8][C:9]1[C:10]([F:19])=[C:11]([C:15]([F:18])=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13].C(N([CH2:25][CH3:26])CC)C>C(Cl)Cl>[F:19][C:10]1[C:9]([N:8]([S:4]([CH2:1][CH2:25][CH3:26])(=[O:6])=[O:5])[S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])=[CH:17][CH:16]=[C:15]([F:18])[C:11]=1[C:12]([OH:14])=[O:13]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 184053523-Amino-2,6-difluorobenzoic acid

생성물 1

HCID 580953482,6-Difluoro-3-(n-(propylsulfonyl)propyl-sulfonamido)benzoic acid수율 74.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Propane-1-sulfonyl chloride (1.225 mL, 10.92 mmol) was added to a mixture of 3-amino-2,6-difluorobenzoic acid (0.573 g, 3.310 mmol), triethylamine (2.030 mL, 14.56 mmol) and CH2Cl2 (17 mL, 0.2M) cooled to 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture was then partitioned between saturated NaHCO3 (100 mL) and ethyl acetate (75 mL). The aqueous layer was washed with ethyl acetate (50 mL) and then acidified with concentrated HCl to a pH of about 1. The acidified aqueous layer was extracted with ethyl acetate (2×50 mL), and the combined ethyl acetate extracts were dried (Na2SO4), filtered and concentrated. The resulting residue was triturated with hexanes to afford 2,6-difluoro-3-(N-(propylsulfonyl)propyl-sulfonamido)benzoic acid as a solid (0.948 g, 74% yield). 1H NMR (400 MHz, d6-DMSO) δ 7.90-7.84 (m, 1H), 7.39-7.34 (m, 1H), 3.73-3.58 (m, 4H), 1.88-1.74 (m, 4H), 1.01 (t, J=7.5 Hz, 6H). m/z (APCI-neg) M-(SO2Pr)=278.1.

후처리

  1. temperatureto warm to room temperature
  2. customThe mixture was then partitioned between saturated NaHCO3 (100 mL) and ethyl acetate (75 mL)
  3. washThe aqueous layer was washed with ethyl acetate (50 mL)
  4. extractionThe acidified aqueous layer was extracted with ethyl acetate (2×50 mL)
  5. dry with materialthe combined ethyl acetate extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was triturated with hexanes

출처 및 근거

ORD 기록
ord-118d9bde901f4307b30d85df75836914
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394795B2

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