Trifluoroacetic acid → HCID 22479108, compound

HRID 1392169Notes

Reaction equation

HRID 1392169 reaction equation
C(OC([N:8]1[CH2:16][C:15]2([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=3)[N:11]([C:12](=[O:34])[N:13]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=3)[C:14]2=[O:25])[CH2:10][CH2:9]1)=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:15]23[C:14](=[O:25])[N:13]([C:26]4[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=4)[C:12](=[O:34])[N:11]2[CH2:10][CH2:9][NH:8][CH2:16]3)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 22479167HCID 22479167, compound

Product 1

HCID 22479108HCID 22479108, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(tert-butoxycarbonyl)-6-(4-bromobenzyl)-8-(3,5-dichlorophenyl)-1,4,8-triazabicyclo[4.3.0]nonane-7,9-dione (0.82 g) in CH2Cl2 (10 mL) was added TFA (0.5 mL). Additional TFA (0.5 mL) was added after 1 hour and 2.5 hours. After 5 hours, the reaction mixture was diluted with CH2Cl2, washed with aqueous NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated to yield the titled compound (0.63 g). MS (m/z) 468 (MH+). mp 92.5° C.

Workup

  1. washwashed with aqueous NaHCO3, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f3dac8e4a40b49588f13bc98d635adbb
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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