2-Bromoethanol → 4-Piperidineacetic acid

HRID 1989879노트

반응식

HRID 1989879 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 15125944-Piperidineacetic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-515b2ec2bac4444ea853a0d8809e944e
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642378B2

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