Trifluoroacetic acid → HCID 75053846, compound

HRID 402199Notes

Reaction equation

HRID 402199 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:18]=[C:17]([O:19][CH:20]3[CH2:38][CH:37]4[N:22]([C:23](=[O:59])[N:24](CC5C=CC(OC)=CC=5)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40]([NH:42][S:43]([C:46]6([CH3:49])[CH2:48][CH2:47]6)(=[O:45])=[O:44])=[O:41])([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:21]3)[C:16]3[C:11](=[C:12]([CH3:62])[C:13]([O:60][CH3:61])=[CH:14][CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClCCl>[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:18]=[C:17]([O:19][CH:20]3[CH2:38][CH:37]4[N:22]([C:23](=[O:59])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40]([NH:42][S:43]([C:46]6([CH3:49])[CH2:48][CH2:47]6)(=[O:45])=[O:44])=[O:41])([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:21]3)[C:16]3[C:11](=[C:12]([CH3:62])[C:13]([O:60][CH3:61])=[CH:14][CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 76674797HCID 76674797, compound

Product 1

HCID 75053846HCID 75053846, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To compound 139 (106 mg, 0.120 mmol) dissolved in dichloromethane (18 mL) were added triethylsilane (38 μL, 0.240 mmol) and TFA (9 mL) and the reaction mixture was stirred at room temperature for 1 hour. The solvents were evaporated and co-evaporated trice with toluene. The residue was dissolved in dichloromethane and the organic phase was washed twice with saturated NaHCO3 solution. The organic phase was dried, filtered, and concentrated and the crude product was purified by flash column chromatography (toluene/ethyl acetate 1:1) to yield the title compound (73 mg, 80%) as a slightly yellow solid. LC-MS purity: >95%. (M+H)+ cald: 765.3. found: 765.7.

Workup

  1. customThe solvents were evaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe organic phase was washed twice with saturated NaHCO3 solution
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe crude product was purified by flash column chromatography (toluene/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-b59b1b7311194e39982d1731e26bef32
Source dataset
uspto-grants-2014_06
Patent number
US08741926B2

Reaction notes

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