(R)-3-Pyrrolidinol → HCID 90042368、化合物

HRID 1050234ノート

反応式

HRID 1050234 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH:17]1[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([N:17]3[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18]3)=[O:16])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 2759337(R)-3-PyrrolidinolHCID 28183884-(4-Bromophenyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 90042368HCID 90042368、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4′-bromo-[1,1′-biphenyl]-4-carboxylic acid (2 g, 7.22 mmol), (R)-pyrrolidin-3-ol (1.3 g, 14.92 mmol), and HATU (5.5 g, 14.46 mmol) were dissolved in DMF (60 mL). To this solution was added TEA (4 ml, 28.7 mmol) and the reaction mixture was stirred under N2 at room temperature for 24 h. Then the volatiles were removed in vacuo and the resulting residue was partitioned between EtOAc and H2O. The organic layer was separated and washed with 1N HCl, saturated NaHCO3, and brine, and then dried over Na2SO4, filtered and concentrated in vacuo. Chromatography of the resulting residue over silica eluting with 3% MeOH in DCM afforded the desired product. LC-MS: calculated for C17H16BrNO2 345.04 observed m/e: 346.09 (M+H)+ (Rt: 1.62/4 min).

後処理

  1. customThen the volatiles were removed in vacuo
  2. customthe resulting residue was partitioned between EtOAc and H2O
  3. customThe organic layer was separated
  4. washwashed with 1N HCl, saturated NaHCO3, and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d288cf4eb0f24f7a9a78fe96fb4471e9
出典データセット
uspto-grants-2016_07
特許番号
US09382243B2

反応ノート

読み込み中…