1-Hydroxybenzotriazole → HCID 68818466, compound

HRID 734328Notes

Reaction equation

HRID 734328 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:17]([O:24][C:25]([N:27]1[CH2:32][CH2:31][NH:30][C@@H:29]([CH3:33])[CH2:28]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN(CC1C=CC=CC=1)CC.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1>C(Cl)Cl.C(Cl)CCl>[CH2:17]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])[C@@H:29]([CH3:33])[CH2:28]1)=[O:26])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 7578289Benzyl (3S)-3-methylpiperazine-1-carboxylateHCID 16212021N-benzyl-N-ethylethanamine;1,4-bis(ethenyl)benzene;styrene

Product 1

HCID 68818466HCID 68818466, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

1-(tert-Butoxycarbonyl)-piperidine4-carboxylic acid (0.53 g), (S)-1-benzyloxycarbonyl-3-methylpiperazine (D19)(0.5 g), HOBt (0.29 g) and diethylaminomethyl polystyrene (1.78 g) were stirred in DCM (30 ml), then EDC (0.53 g) was added and the reaction was stirred at rt ovemight. The mixture was filtered and washed with saturated sodium hydrogen carbonate solution (3×50 ml) and brine (30 ml). The organic layer was dried (MgSO4) and evaporated to give a crude yellow oil which was purified by chromatography [silica gel; 0-100% ethyl acetate/hexane) to give the tide compound (D20) as a clear oil which crystallised on standing (0.88 g).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with saturated sodium hydrogen carbonate solution (3×50 ml) and brine (30 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customto give a crude yellow oil which
  6. customwas purified by chromatography [silica gel
  7. custom0-100% ethyl acetate/hexane) to give the tide compound (D20) as a clear oil which
  8. customcrystallised

Sources & evidence

ORD record
ord-a9d13b3a961346c3b33f3099d5c8fce9
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

Loading…