Trifluoroacetic acid → HCID 70664463, compound

HRID 1186082Notes

Reaction equation

HRID 1186082 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16]2[CH:17]=[C:18]([C:21]3[C:22]4[CH:49]=[C:48]([Cl:50])[CH:47]=[CH:46][C:23]=4[N:24]([CH2:37][C:38]4[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=4)[C:25](=[O:36])[C@H:26]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[Cl:35])[N:27]=3)[CH:19]=[CH:20][C:15]=2[NH:14][C:13]1=[O:51])(C(C)(C)C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:50][C:48]1[CH:47]=[CH:46][C:23]2[N:24]([CH2:37][C:38]3[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=3)[C:25](=[O:36])[C@H:26]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[N:27]=[C:21]([C:18]3[CH:19]=[CH:20][C:15]4[NH:14][C:13](=[O:51])[N:12]([CH2:11][CH2:10][CH2:9][OH:8])[C:16]=4[CH:17]=3)[C:22]=2[CH:49]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid3×HCID 70664288HCID 70664288, compound

Product 1

HCID 70664463HCID 70664463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-5-(3-(3-((tert-Butyldimethylsilyl)oxy)propyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-7-chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (100 mg, 0.134 mmol) was dissolved in DCM (˜10 mL) and treated with 0.5 mL trifluoroacetic acid. After 1.5 hr, the reaction was ˜30% complete by TLC. Another 0.5 mL trifluoroacetic acid was added. After another 1.5 hr, another 0.5 mL trifluoroacetic acid was added. This mixture was allowed to stir at room temperature overnight. It was still mostly starting material by TLC. The solvent was evaporated and azeotroped 3× from DCM. 4 M HCl in 1,4-dioxane (3 mL) was added. This mixture was stirred at RT under nitrogen for 1 hr. TLC (quenched in Et3N-DCM) showed all starting material had converted. The solvent was evaporated to give the title compound as a yellow oil, which was used in the next step without further purification.

Workup

  1. waitAfter another 1.5 hr
  2. customThe solvent was evaporated
  3. customazeotroped 3× from DCM
  4. addition4 M HCl in 1,4-dioxane (3 mL) was added
  5. stirringThis mixture was stirred at RT under nitrogen for 1 hr
  6. customTLC (quenched in Et3N-DCM)
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-06526241ba9f40dfbd56c9a3734b4adf
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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