HCID 22479245, compound → HCID 22479230, compound

HRID 2182614Notes

Reaction equation

HRID 2182614 reaction equation
C(OC([N:8]1[CH2:16][CH2:15][CH2:14][C:13]2([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=3)[N:9]1[C:10](=[O:34])[N:11]([C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=1)[C:12]2=[O:25])=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C:13]23[C:12](=[O:25])[N:11]([C:26]4[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=4)[C:10](=[O:34])[N:9]2[NH:8][CH2:16][CH2:15][CH2:14]3)=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 22479245HCID 22479245, compound

Product 1

HCID 22479230HCID 22479230, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

2-(tert-Butoxycarbonyl)-6-(4-bromobenzyl)-8-(3,5-dichlorophenyl)-1,2,8-triazabicyclo[4.3.0]nonane-7,9-dione (260 mg) was dissolved in TFA/CH2Cl2 (50%, 5 mL) and stirred at room temperature for 3 hours. The reaction mixture was then concentrated in vacuo, redissolved in CH2Cl2 (5 mL) and DIEA (0.22 mL) was added. The mixture was stirred at room temperature for 30 minutes and was shaken with CH2Cl2/H2O. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layer was dried over MgSO4, filtered and concentrated. The residue was recrystallized from EtOAc/hexane to give the titled compound (180 mg). MS (m/z) 470 (M+).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionredissolved in CH2Cl2 (5 mL)
  3. additionDIEA (0.22 mL) was added
  4. stirringThe mixture was stirred at room temperature for 30 minutes
  5. stirringwas shaken with CH2Cl2/H2O
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with CH2Cl2
  8. dry with materialThe combined organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-a881e7c445bb4a3fa513bff90289950a
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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