Trifluoroacetic acid → HCID 90370239, compound

HRID 2175995Notes

Reaction equation

HRID 2175995 reaction equation
C(OC([NH:8][CH2:9][CH2:10][N:11]([CH2:17][C:18]1[CH:19]=[C:20]([CH:54]=[CH:55][CH:56]=1)[C:21]([NH:23][C:24]1[S:25][C:26]2[CH2:53][CH2:52][CH2:51][CH2:50][C:27]=2[C:28]=1[C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]2[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][CH:41]=2)=[CH:34][CH:33]=1)=[O:30])=[O:22])[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][N:11]([CH2:17][C:18]1[CH:19]=[C:20]([CH:54]=[CH:55][CH:56]=1)[C:21]([NH:23][C:24]1[S:25][C:26]2[CH2:53][CH2:52][CH2:51][CH2:50][C:27]=2[C:28]=1[C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]2[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][CH:41]=2)=[CH:34][CH:33]=1)=[O:30])=[O:22])[CH:12]([CH2:13][CH3:14])[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90370279HCID 90370279, compound

Product 1

HCID 90370239HCID 90370239, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 240 mg of methyl 4-(2-{4-[({2-[(3-{[{2-[(tert-butoxycarbonyl)amino]ethyl}(pentan-3-yl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate and 5.0 mL of methylene chloride was added 3.0 mL of TFA under ice cooling, followed by stirring for 1 hour at the same temperature and then stirring for 5 hours at room temperature. The reaction mixture was concentrated under reduced pressure, chloroform and a saturated aqueous sodium hydrogen carbonate solution were added thereto, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure, thereby obtaining 210 mg of methyl 4-(2-{4-[({2-[(3-{[(2-aminoethyl)(pentan-3-yl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate.

Workup

  1. stirringstirring for 5 hours at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure, chloroform
  3. additiona saturated aqueous sodium hydrogen carbonate solution were added
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0e74aed9753d444bb683cee9f8ff28ae
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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