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Boron Trichloride → 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-(4-(morpholin-4-ylmethyl)phenyl)isoxazole-3-carboxamide

HRID 1891153
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HRID 1891153 반응식
B(Cl)(Cl)Cl.[CH2:5]([NH:7][C:8]([C:10]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)=[C:13]([C:28]2[CH:33]=[C:32]([Cl:34])[C:31]([O:35]CC3C=CC=CC=3)=[CH:30][C:29]=2[O:43]CC2C=CC=CC=2)[O:12][N:11]=1)=[O:9])[CH3:6].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:5]([NH:7][C:8]([C:10]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:19][CH:20]=2)=[C:13]([C:28]2[CH:33]=[C:32]([Cl:34])[C:31]([OH:35])=[CH:30][C:29]=2[OH:43])[O:12][N:11]=1)=[O:9])[CH3:6]
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참가 물질

5

반응물 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 247741945-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

생성물 1

HCID 1355254165-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-(4-(morpholin-4-ylmethyl)phenyl)isoxazole-3-carboxamide수율 64.3%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

BCl3 (1M sol. in CH2Cl2, 3.87 ml, 3.87 mmol) was added dropwise to a solution of the crude 5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide (810 mg, ˜1.29 mmol) in CH2Cl2 (30 ml) at 0° C. The reaction was then allowed to reach RT. Saturated aqueous NaHCO3 (40 ml) was then added slowly and the resultant mixture concentrated in vacuo. This was then partitioned between EtOAc (3×50 ml) and water (50 ml). The combined, dried (Na2SO4) organics were evaporated in vacuo. Flash chromatography eluting with CH2Cl2-10% MeOH/1% NH3/CH2Cl2 afforded 5-(5-Chloro-2,4-dihydroxy-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide (380 mg, 64% over 2 steps) as a yellow foam, LC/MS: RT=1.751 min. 458.2 (MH+).

후처리

  1. customto reach RT
  2. concentrationthe resultant mixture concentrated in vacuo
  3. customThis was then partitioned between EtOAc (3×50 ml) and water (50 ml)
  4. dry with materialdried (Na2SO4)
  5. customorganics were evaporated in vacuo
  6. washFlash chromatography eluting with CH2Cl2-10% MeOH/1% NH3/CH2Cl2

출처 및 근거

ORD 기록
ord-ebcc5b2ac39148deb62940c194abd882
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08507480B2

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