HCID 131721986, compound → HCID 70107440, compound

HRID 381496Notes

Reaction equation

HRID 381496 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:44])/[CH:24]=[CH:25]/[C:26]3[CH:43]=[CH:42][C:29]([O:30][CH2:31][CH2:32][N:33](C)[C:34](=O)OC(C)(C)C)=[CH:28][CH:27]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:44])/[CH:24]=[CH:25]/[C:26]3[CH:27]=[CH:28][C:29]([O:30][CH2:31][CH2:32][NH:33][CH3:34])=[CH:42][CH:43]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 131721986HCID 131721986, compound

Product 1

HCID 70107440HCID 70107440, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 190 (0.33 g, 0.55 mmol) in DCM (30 mL) was treated with zinc bromide (0.63 g, 5 equiv.) for 16 hours at 30° C. A gummy solid was formed. Extraction with DCM:MeOH, washing with water, drying over Na2SO4 and recrystallization from iPrOH gave the title compound as white crystals in a 98% yield.

Workup

  1. customA gummy solid was formed
  2. extractionExtraction with DCM
  3. washMeOH, washing with water
  4. dry with materialdrying over Na2SO4 and recrystallization from iPrOH

Sources & evidence

ORD record
ord-717643529b994072ad4064d7ae76983e
Source dataset
uspto-grants-2001_10
Patent number
US06306870B1

Reaction notes

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