2-Bromoethanol → 4-Piperidineacetic acid

HRID 1989879ノート

反応式

HRID 1989879 の反応式
BrCCO.Cl.C1([CH:12]([CH:16]2[CH2:21][CH2:20][N:19](C3C=CC(NC(C4C=CC=CC=4C4C=CC(C(F)(F)F)=CC=4)=O)=CC=3)[CH2:18][CH2:17]2)[C:13]([OH:15])=[O:14])C=CC=CC=1>CN(C=O)C>[NH:19]1[CH2:20][CH2:21][CH:16]([CH2:12][C:13]([OH:15])=[O:14])[CH2:17][CH2:18]1

参加物

4

反応物 2

HCID 108982-BromoethanolHCID 68521936alpha-Phenyl-1-[4-[[[4'-(trifluoromethyl)[1,1'-biphenyl]-2-yl]carbonyl]amino]phenyl]-4-piperidineacetic acid monohydrochloride

生成物 1

HCID 15125944-Piperidineacetic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

2-Bromoethanol (1.2 equiv, 0.00010 mol) was added to a mixture of intermediate (24) (0.000084 mol) in DMF (5 ml) and CsCO3 (0.00018 mol) and the reaction mixture was stirred for 3 hours at 70° C. The solvent was evaporated. The residue was partitioned between water and DCM. The extract's solvent was evaporated. The residue was purified by HPLC (Waters column, with Xterra MS C18; eluent: [(0.5% NH4OAc in H2O)/CH3CN 90/10)]/CH3CN (0 minutes) 85/15, (10 minutes) 10/90, (16 minutes) 0/100, (18.10-20.00 minutes) 85/15). The product fractions were collected and the organic solvent was evaporated. The aqueous concentrates were extracted and the extract's solvent was evaporated, yielding 4-piperidineacetic acid, α-phenyl-1-[4-[[[4′-(trifluoromethyl)[1,1′-biphenyl]-2-yl]carbonyl]amino]phenyl]-, 2-hydroxyethyl ester (compound 134).

後処理

  1. customThe solvent was evaporated
  2. customThe residue was partitioned between water and DCM
  3. customThe extract's solvent was evaporated
  4. customThe residue was purified by HPLC (Waters column
  5. customCH3CN (0 minutes) 85/15, (10 minutes) 10/90, (16 minutes) 0/100, (18.10-20.00 minutes) 85/15
  6. customThe product fractions were collected
  7. customthe organic solvent was evaporated
  8. extractionThe aqueous concentrates were extracted
  9. customthe extract's solvent was evaporated

出典と根拠

ORDレコード
ord-515b2ec2bac4444ea853a0d8809e944e
出典データセット
uspto-grants-2010_01
特許番号
US07642378B2

反応ノート

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