Hydrochloric Acid → N1-(4-(3-aminophenyl)thiazol-2-yl)-N8-hydroxyoctanediamide

HRID 243627노트

반응식

HRID 243627 반응식
Cl.[NH2:2][OH:3].CO.[OH-].[K+].C[O:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=2)[N:24]=1)=[O:18].[OH-].[K+].Cl>O>[NH2:31][C:27]1[CH:26]=[C:25]([C:23]2[N:24]=[C:20]([NH:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([NH:2][OH:3])=[O:9])[S:21][CH:22]=2)[CH:30]=[CH:29][CH:28]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 23689386Potassium hydroxide methanolHCID 44550930octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide methyl ester

생성물 1

HCID 24178404N1-(4-(3-aminophenyl)thiazol-2-yl)-N8-hydroxyoctanediamide수율 44%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

To a solution of hydroxylamine hydrochloride (0.958 g, 13.8 mmol) in MeOH-KOH (0.772 g, 13.8 mmol) was added at 40° C. for 10 minutes. The reaction mixture was cooled to 0° C. and filtered. Compound 20 (0.250 g, 0.69 mmol) was added to the filtrate followed by KOH (50 mg, 0.89 mmol) at room temperature. After 2 hours, water (20 ml) was added, followed by 1 N HCl until pH reached 6.5. The reaction mixture was extracted with EtOAc, and organic layer was washed with brine, dried over Na2SO4 and filtered. The solvent was removed by rotary evaporation. The crude solid was purified by preparative HPLC to give compound 23 (0.110 g, 43.9%). 1H NMR (300 MHz, CD3OD) δ 7.98 (1H, d, J=7.8 Hz), 7.90 (1H, s), 7.55 (1H, t, J=7.8 Hz), 7.51 (1H, s), 7.29 (1H, dd, J=7.8, 1.2 Hz), 2.51 (2H, t, J=7.2 Hz), 2.11 (2H, t, J=7.2 Hz), 1.74 (2H, t, J=7.0 Hz), 1.65 (2H, t, J=7.0 Hz), 1.50-1.35 (4H, m). 13C NMR (100 MHz, CD3OD) δ 172.1, 158.0, 147.4, 136.3, 129.7, 125.1, 120.8, 119.2, 108.5, 34.6, 28.0, 27.9, 24.7, 24.3.

후처리

  1. filtrationfiltered
  2. extractionThe reaction mixture was extracted with EtOAc, and organic layer
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed by rotary evaporation
  7. customThe crude solid was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-0537ac75dd924afb9ff738e965e9a7c6
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653278B2

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