N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamide → HCID 117942080、化合物

HRID 1499102ノート

反応式

HRID 1499102 の反応式
C1(C)C=CC(S(N[C@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.[Br:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])=[C:30]([N:40]2[CH:44]=[CH:43][C:42]([CH3:45])=[N:41]2)[CH:29]=1.C([O-])=O.[K+]>O.C(#N)C.C[Ir-4](Cl)(C)(C)(C)(C)C1C=CC=C1>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([C@@H:34]([OH:39])[C:35]([F:38])([F:37])[F:36])=[C:30]([N:40]2[CH:44]=[CH:43][C:42]([CH3:45])=[N:41]2)[CH:29]=1

参加物

7

反応物 3

HCID 2734565N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamideHCID 2735122Potassium FormateHCID 1179421121-(4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone

生成物 1

HCID 117942080HCID 117942080、化合物

試薬・触媒・溶媒 3

HCID 178477776HCID 178477776、化合物触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

Pentamethylcyclopentadienyl iridium (III) chloride dimer (CAS#12354-84-6) (10.4 mg) and (1R,2R)-(−)-N-(4-toluene sulfonyl)-1,2-diphenyl ethylene diamine (CAS#144222-34-4) (9.2 mg) were combined in water (120 mL), then heated to 50° C. for 5 h to provide the “Iridium complex.” 1-[4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethanone (16 g, 48 mmol) was dissolved in acetonitrile (120 mL) to which the Iridium complex and potassium formate (3.1 g, 3.7 mmol) were added. The reaction mixture was heated to 50° C. for 8 h. The reaction mixture was then cooled to RT, partitioned between water and EtOAc, and extracted. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Recrystallization from hot heptane (200 mL) provided the title compound.

後処理

  1. customto provide the “Iridium complex
  2. additionwere added
  3. temperatureThe reaction mixture was heated to 50° C. for 8 h
  4. temperatureThe reaction mixture was then cooled to RT
  5. custompartitioned between water and EtOAc
  6. extractionextracted
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customRecrystallization from hot heptane (200 mL)

出典と根拠

ORDレコード
ord-89e44f85a3e4496ca1b80e58d5cb93fa
出典データセット
uspto-grants-2015_12
特許番号
US09199994B2

反応ノート

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