(S)-styrene oxide → HCID 22466446, compound

HRID 1934587Notes

Reaction equation

HRID 1934587 reaction equation
[NH2:1][CH:2]([CH3:50])[CH:3]([N:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]5[CH2:35][O:34][C:33]([C:42]6[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=6[F:49])([CH2:36][N:37]6[CH:41]=[N:40][CH:39]=[N:38]6)[O:32]5)=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH:7]=[N:6]1)[CH3:4].[C:51]1([C@H:57]2[CH2:59][O:58]2)[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CC(O)C>[F:49][C:43]1[CH:44]=[C:45]([F:48])[CH:46]=[CH:47][C:42]=1[C:33]1([CH2:36][N:37]2[CH:41]=[N:40][CH:39]=[N:38]2)[O:32][CH:31]([CH2:30][O:29][C:26]2[CH:25]=[CH:24][C:23]([N:20]3[CH2:19][CH2:18][N:17]([C:14]4[CH:13]=[CH:12][C:11]([N:8]5[CH:7]=[N:6][N:5]([CH:3]([CH3:4])[CH:2]([NH:1][CH2:59][CH:57]([OH:58])[C:51]6[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=6)[CH3:50])[C:9]5=[O:10])=[CH:16][CH:15]=4)[CH2:22][CH2:21]3)=[CH:28][CH:27]=2)[CH2:35][O:34]1

Participants

4

Reactant 2

HCID 114946(S)-styrene oxide2×HCID 77776170HCID 77776170, compound

Product 1

HCID 22466446HCID 22466446, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of compound (37) (0.0043 mol) and (S)-phenyl oxirane (0.005 mol) in 2-propanol (50 ml) was stirred and refluxed overnight. (S)-phenyl oxirane (0.005 mol) was added again. The mixture was stirred and refluxed for 3 hours. The solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1). The pure fractions were collected and the solvent was evaporated. The residue was triturated in DIPE, filtered off and dried, yielding 1.6 g (47%) of [2S-[2α,4α[(S*,R*)(R*)]]]4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[2[(2-hydroxy-2-phenylethyl)amino]-1-methylpropyl]-3H-1,2,4-triazol-3-one (compound 81).

Workup

  1. temperaturerefluxed overnight
  2. stirringThe mixture was stirred
  3. temperaturerefluxed for 3 hours
  4. customThe solvent was evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was triturated in DIPE
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-43690f4af3c249dcbdeaa95d4c0f58e5
Source dataset
uspto-grants-2002_05
Patent number
US06384030B1

Reaction notes

Loading…