HCID 86647503, compound → HCID 59571230, compound

HRID 389218Notes

Reaction equation

HRID 389218 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18](=[O:35])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]C=C)[C@H:15]([C:36]([NH:38][C@:39]3([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:41][C@H:40]3[CH:42]=[CH2:43])=[O:37])[CH2:14]2)=[CH:4][C:3]=1[O:49][CH3:50]>ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]3[C:18](=[O:35])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:43]=[CH:42][C@@H:40]4[CH2:41][C@@:39]4([C:44]([O:46][CH2:47][CH3:48])=[O:45])[NH:38][C:36](=[O:37])[C@@H:15]3[CH2:14]2)=[CH:4][C:3]=1[O:49][CH3:50]

Participants

3

Reactant 1

HCID 86647503HCID 86647503, compound

Product 1

HCID 59571230HCID 59571230, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Step 3 (200 mg, 0.264 mmol) in dichloromethane (26 mL) was bubbled with nitrogen gas for 30 minutes. Zhan catalyst 1B (19.4 mg, 0.026 mmol) was added, and the reaction mixture was heated at reflux under nitrogen for 2 hours. The mixture was concentrated and chromatographed on silica gel 60, eluting with 5% to 75% EtOAc in hexane to give the title product (135 mg). LRMS (ESI) m/z 729.3 [(M+H)+; calcd for C35H46BrN4O8: 729.3].

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 2 hours
  3. concentrationThe mixture was concentrated
  4. customchromatographed on silica gel 60
  5. washeluting with 5% to 75% EtOAc in hexane

Sources & evidence

ORD record
ord-4b94bd0c37a74bb5a935abf9919c9f06
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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