Pyrrolidine → HCID 86717254, compound

HRID 1482764Notes

Reaction equation

HRID 1482764 reaction equation
C(OC(=O)[NH:6][C@@H:7]([CH:64]([CH3:66])[CH3:65])[C:8]([NH:10][C@@H:11]([CH3:63])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH2:22][CH:23]3[CH:29]=[N:28][C:27]4[CH:30]=[C:31]([O:36][CH2:37][CH2:38][CH2:39][O:40][C:41]5[C:42]([O:59][CH3:60])=[CH:43][C:44]6[C:50](=[O:51])[N:49]7[CH:52]=[C:53]([CH:55]8[CH2:57][CH2:56]8)[CH2:54][CH:48]7[CH:47]=[N:46][C:45]=6[CH:58]=5)[C:32]([O:34][CH3:35])=[CH:33][C:26]=4[C:25](=[O:61])[N:24]3[CH:62]=2)=[CH:17][CH:16]=1)=[O:13])=[O:9])C=C.N1CCCC1>C(Cl)Cl.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>[NH2:6][C@@H:7]([CH:64]([CH3:66])[CH3:65])[C:8]([NH:10][C@@H:11]([CH3:63])[C:12]([NH:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH2:22][CH:23]3[CH:29]=[N:28][C:27]4[CH:30]=[C:31]([O:36][CH2:37][CH2:38][CH2:39][O:40][C:41]5[C:42]([O:59][CH3:60])=[CH:43][C:44]6[C:50](=[O:51])[N:49]7[CH:52]=[C:53]([CH:55]8[CH2:57][CH2:56]8)[CH2:54][CH:48]7[CH:47]=[N:46][C:45]=6[CH:58]=5)[C:32]([O:34][CH3:35])=[CH:33][C:26]=4[C:25](=[O:61])[N:24]3[CH:62]=2)=[CH:19][CH:20]=1)=[O:13])=[O:9]

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 86717255HCID 86717255, compound

Product 1

HCID 86717254HCID 86717254, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

The starting material 16 (170 mg, 0.185 mmol) was dissolved in dry CH2Cl2 (5 mL) in a round bottom flask filled with argon, before pyrrolidine (41 μL, 0.21 mmol) was added. The flask was purged/refilled three times with argon before Pd(PPh3)4 (14 mg, 0.084 mmol) was added and the flushing operation repeated. After 1 hour, complete consumption of starting material was observed (the reaction was followed by LC/MS) and Et2O (50 mL) was added to the reaction mixture which was allowed to stir until all the product had crashed out of solution. The solid was filtered through a sintered funnel and washed twice with Et2O (2×25 mL). The collecting flask was replaced and the isolated solid was dissolved in CHCl3 (100 mL or until all the product had passed through the sintered funnel). The volatiles were then removed by rotary evaporation under reduced pressure to afford the crude product 17 which was used directly in the next step (168 mg). LC/MS method 2 (2.70 min (ES+) m/z (relative intensity) 830.27 ([M+H]+, 50), 660.13 (80), 171.15 (100)).

Workup

  1. additionwas added
  2. additionwas added
  3. customcomplete consumption of starting material
  4. additionwas added to the reaction mixture which
  5. filtrationThe solid was filtered through a sintered funnel
  6. washwashed twice with Et2O (2×25 mL)
  7. dissolutionthe isolated solid was dissolved in CHCl3 (100 mL
  8. customThe volatiles were then removed by rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-39a4b255852a4a8aafb3ce5cb528d84f
Source dataset
uspto-grants-2016_08
Patent number
US09415117B2

Reaction notes

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