Piperidine → HCID 44549611, compound

HRID 1924375Notes

Reaction equation

HRID 1924375 reaction equation
CCN(C(C)C)C(C)C.Cl.[NH2:11][C@H:12]([C:16]([N:18]1[CH2:26][C@H:25]([O:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[C:35]([CH:38]=[CH2:39])[CH:36]=3)[CH:31]=[CH:30][N:29]=2)[CH2:24][C@H:19]1[C:20]([O:22][CH3:23])=[O:21])=[O:17])[CH:13]([CH3:15])[CH3:14].C([N:57]=[C:58]=[S:59])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.N1CCCCC1>C(Cl)Cl.CO>[NH2:57][C:58]([NH:11][C@H:12]([C:16]([N:18]1[CH2:26][C@H:25]([O:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[C:35]([CH:38]=[CH2:39])[CH:36]=3)[CH:31]=[CH:30][N:29]=2)[CH2:24][C@H:19]1[C:20]([O:22][CH3:23])=[O:21])=[O:17])[CH:13]([CH3:15])[CH3:14])=[S:59]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 4154759Fmoc isothiocyanateHCID 44549476HCID 44549476, compound

Product 1

HCID 44549611HCID 44549611, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

iPr2NEt (2 eq) was added to a suspension of hydrochloride from Step 2 in DCM at 0° C., and the resulting clear solution was immediately added to a solution of FMOC-isothiocyanate (1.1 eq) in DCM at 0° C. The resulting mixture was stirred at RT for 30 min and then treated with a 20% solution of piperidine in MeOH. After 3 h, the volatiles were removed under reduced pressure and the residue was purified by SiO2 gel chromatography (gradient elution, hexane/EtOAc=8/2 to DCM/MeOH=95/5) to give the title compound as a pale yellow foam. MS (ES+) C23H28N4O4S requires: 456. Found: 457 (M+H+).

Workup

  1. waitAfter 3 h
  2. customthe volatiles were removed under reduced pressure
  3. customthe residue was purified by SiO2 gel chromatography (gradient elution, hexane/EtOAc=8/2 to DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-da5c0ceeb5bf4e44814cdf7280e9bd17
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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