Piperidine → HCID 118114382, compound

HRID 1778418Notes

Reaction equation

HRID 1778418 reaction equation
N1CCCCC1.[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH2:17][C@H:18]4[CH:24]=[N:23][C:22]5[CH:25]=[C:26]([O:31][CH2:32][CH2:33][CH2:34][O:35][C:36]6[C:37]([O:84][CH3:85])=[CH:38][C:39]7[C:45](=[O:46])[N:44]8[CH:47]=[C:48]([C:50]#[C:51][CH2:52][NH:53][C:54](=[O:82])[C@@H:55]([NH:57][C:58](=[O:81])[C@H:59]([NH:63]C(=O)OCC9C%10C=CC=CC=%10C%10C9=CC=CC=%10)[CH:60]([CH3:62])[CH3:61])[CH3:56])[CH2:49][C@H:43]8[CH:42]=[N:41][C:40]=7[CH:83]=6)[C:27]([O:29][CH3:30])=[CH:28][C:21]=5[C:20](=[O:86])[N:19]4[CH:87]=3)=[CH:15][C:10]=2[O:9][CH2:8]1>CN(C=O)C.C(Cl)Cl>[NH2:63][C@@H:59]([CH:60]([CH3:62])[CH3:61])[C:58]([NH:57][C@@H:55]([CH3:56])[C:54]([NH:53][CH2:52][C:51]#[C:50][C:48]1[CH2:49][C@H:43]2[CH:42]=[N:41][C:40]3[CH:83]=[C:36]([O:35][CH2:34][CH2:33][CH2:32][O:31][C:26]4[C:27]([O:29][CH3:30])=[CH:28][C:21]5[C:20](=[O:86])[N:19]6[CH:87]=[C:16]([C:14]7[CH:13]=[CH:12][C:11]8[O:7][CH2:8][O:9][C:10]=8[CH:15]=7)[CH2:17][C@H:18]6[CH:24]=[N:23][C:22]=5[CH:25]=4)[C:37]([O:84][CH3:85])=[CH:38][C:39]=3[C:45](=[O:46])[N:44]2[CH:47]=1)=[O:82])=[O:81]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 131734808HCID 131734808, compound

Product 1

HCID 118114382HCID 118114382, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Excess piperidine was added (0.01 mL, 0.1 mmol) to a solution of SEM-dilactam 11d (1 mg, 0.0009 mmol) in DMF (0.1 mL). The mixture was allowed to stir at room temperature for 20 min, at which point the reaction had gone to completion (monitored by LC/MS). The reaction mixture was diluted with CH2Cl2 (1 mL) and the organic phase was washed with H2O (3×1 mL) until complete piperidine removal. The organic phase was dried over MgSO4, filtered and excess solvent removed by rotary evaporation under reduced pressure to afford crude material 12d. LC/MS (1.917 min (ES+)). m/z: 872.2 [M+H]+

Workup

  1. washthe organic phase was washed with H2O (3×1 mL) until complete piperidine removal
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customexcess solvent removed by rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-ef7785ec57ef4f999e18fbc91fde68b5
Source dataset
uspto-grants-2016_02
Patent number
US09266894B2

Reaction notes

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