Pyrrolidine → HCID 117629188, compound

HRID 1050881Notes

Reaction equation

HRID 1050881 reaction equation
C(OC([NH:7][C@@H:8]([CH:72]([CH3:74])[CH3:73])[C:9]([NH:11][C@@H:12]([CH3:71])[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH2:23][C@H:24]3[CH:30]=[N:29][C:28]4[CH:31]=[C:32]([O:37][CH2:38][CH2:39][CH2:40][O:41][C:42]5[C:43]([O:67][CH3:68])=[CH:44][C:45]6[C:51](=[O:52])[N:50]7[CH:53]=[C:54]([C:56]8[CH:65]=[CH:64][C:59]([C:60]([O:62][CH3:63])=[O:61])=[CH:58][CH:57]=8)[CH2:55][C@H:49]7[CH:48]=[N:47][C:46]=6[CH:66]=5)[C:33]([O:35][CH3:36])=[CH:34][C:27]=4[C:26](=[O:69])[N:25]3[CH:70]=2)=[CH:18][CH:17]=1)=[O:14])=[O:10])=O)C=C.N1CCCC1>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:7][C@@H:8]([CH:72]([CH3:74])[CH3:73])[C:9]([NH:11][C@@H:12]([CH3:71])[C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH2:23][C@H:24]3[CH:30]=[N:29][C:28]4[CH:31]=[C:32]([O:37][CH2:38][CH2:39][CH2:40][O:41][C:42]5[C:43]([O:67][CH3:68])=[CH:44][C:45]6[C:51](=[O:52])[N:50]7[CH:53]=[C:54]([C:56]8[CH:57]=[CH:58][C:59]([C:60]([O:62][CH3:63])=[O:61])=[CH:64][CH:65]=8)[CH2:55][C@H:49]7[CH:48]=[N:47][C:46]=6[CH:66]=5)[C:33]([O:35][CH3:36])=[CH:34][C:27]=4[C:26](=[O:69])[N:25]3[CH:70]=2)=[CH:20][CH:21]=1)=[O:14])=[O:10]

Participants

6

Reactant 2

HCID 31268PyrrolidineHCID 117629303HCID 117629303, compound

Product 1

HCID 117629188HCID 117629188, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 178527696HCID 178527696, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8 (43 mg) in anhydrous dichloromethane (3 mL) was added Ph3P (0.5 mg, 0.002 mmol), pyrolidine (7 μL, 0.082 mmol) and tetrakis palladium (1.1 mg, 0.001 mmol). After approximately 30 minutes, the reaction mixture was aspirated onto a 1 mm radial chromatotron plate and eluted with 5% and then 10% methanol in dichloromethane. The major band was collected and concentrated under reduced pressure to give 22 mg (56%) of 9: MS (ES+) m/z 952.5 [M+H]+.

Workup

  1. washeluted with 5%
  2. customThe major band was collected
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b8fce60aceb4f93a1ff5559c6ce0193
Source dataset
uspto-grants-2016_07
Patent number
US09387259B2

Reaction notes

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