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Ethanol → N-(3,4-Dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-4'-(2-oxazolyl)-2'-(2-oxazolylmethyl)[1,1'-biphenyl]-2-sulfonamide

HRID 1457187
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HRID 1457187 반응식
B([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([C:20]1[O:24][N:23]=[C:22]([CH3:25])[C:21]=1[CH3:26])[CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])(=[O:12])=[O:11])(O)O.Br[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[O:35][CH:36]=[CH:37][N:38]=2)=[CH:30][C:29]=1[CH2:39][C:40]1[O:41][CH:42]=[CH:43][N:44]=1.CCO.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][C:22]1[C:21]([CH3:26])=[C:20]([N:13]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[S:10]([C:5]2[C:4]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[O:35][CH:36]=[CH:37][N:38]=4)=[CH:30][C:29]=3[CH2:39][C:40]3[O:41][CH:42]=[CH:43][N:44]=3)=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:12])=[O:11])[O:24][N:23]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 107862242-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamideHCID 221036352-[4-Bromo-3-(2-oxazolylmethyl)phenyl]oxazole

생성물 1

HCID 22103666N-(3,4-Dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-4'-(2-oxazolyl)-2'-(2-oxazolylmethyl)[1,1'-biphenyl]-2-sulfonamide

시약·촉매·용매

3
HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
75 °C

실험 절차

To a solution of 2-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-benzenesulfonamide (472 mg, 1.3 mmol, prepared as described in Step (B) of Example 1), the title compound of Step (D) of this Example (250 mg, 0.82 mmol) in 8 ml of toluene and 6.4 ml of 95% EtOH under argon, tetrakis(triphenylphosphine)palladium(0) (95 mg, 0.082 mmol) was added and followed by 4.8 ml of 2M aq. sodium carbonate. The reaction mixture was heated at 75° C. for 4 hrs, cooled and diluted with 50 ml of EtOAc. The organic liquid was separated and washed with 10 ml H2O and 10 ml brine, dried and concentrated. The residue was chromatographed on silica gel using 1:2 hexane/EtOAc to afford the title compound of this step (47 mg, 10%) as a colorless gum. Rf=0.17, silica gel, 1:2 Hexane/EtOAc.

후처리

  1. temperaturecooled
  2. customThe organic liquid was separated
  3. washwashed with 10 ml H2O and 10 ml brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using 1:2 hexane/EtOAc

출처 및 근거

ORD 기록
ord-0b196e033b5d493bb9d59bcbe6db6779
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05846990

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