Trifluoroacetic acid → HCID 59223146, compound

HRID 539142Notes

Reaction equation

HRID 539142 reaction equation
[CH2:1]([C@H:8]1[NH:23][C:22](=[O:24])[C@@H:21]([CH3:25])[NH:20][C:19](=[O:26])[CH2:18][C@@H:17](/[CH:27]=[CH:28]/[CH2:29][CH2:30][S:31]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:16][C:15](=[O:51])[CH2:14][NH:13][C:12](=[O:52])[C@@H:11]([CH:53]([CH3:55])[CH3:54])[NH:10][C:9]1=[O:56])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([C@H:8]1[NH:23][C:22](=[O:24])[C@@H:21]([CH3:25])[NH:20][C:19](=[O:26])[CH2:18][C@@H:17](/[CH:27]=[CH:28]/[CH2:29][CH2:30][SH:31])[O:16][C:15](=[O:51])[CH2:14][NH:13][C:12](=[O:52])[C@@H:11]([CH:53]([CH3:55])[CH3:54])[NH:10][C:9]1=[O:56])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59223148HCID 59223148, compound

Product 1

HCID 59223146HCID 59223146, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 15 (9 mg, 0.012 mmol) in CH2Cl2 (500 □L) Et3SiH (3.83 μL, 0.024 mmol) and TFA (60 μL) were added. After 15 minutes stirring the solvent was removed in vacuo and the residue was purified by flash column chromatography on silica gel (2-7% MeOH/CH2Cl2) to give thiol 16 (2.3 mg, 0.0043 mmol, 36%) as a white solid: Rf 0.58 MeOH/CH2Cl2 (1:9); LRMS (ES+) m/z 555.4 (100%, [M+Na]+).

Workup

  1. customwas removed in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel (2-7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6c0b40bf536046e982d3419edcfeb850
Source dataset
uspto-grants-2014_10
Patent number
US08865655B2

Reaction notes

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