Trifluoroacetic acid → HCID 25152743, compound

HRID 539138Notes

Reaction equation

HRID 539138 reaction equation
[OH:1][C@H:2]1[CH2:17][C:16](=[O:18])[O:15][O:14][C@H:13](/[CH:19]=[CH:20]/[CH2:21][CH2:22][S:23]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:12][C:11](=[O:43])[NH:10][C@H:9]([CH:44]([CH3:46])[CH3:45])[C:8](=[O:47])[NH:7][C@H:6]([CH3:48])[C:5](=[O:49])[NH:4][C@@H:3]1[CH:50]([CH3:52])[CH3:51].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:1][C@H:2]1[CH2:17][C:16](=[O:18])[O:15][O:14][C@H:13](/[CH:19]=[CH:20]/[CH2:21][CH2:22][SH:23])[CH2:12][C:11](=[O:43])[NH:10][C@H:9]([CH:44]([CH3:46])[CH3:45])[C:8](=[O:47])[NH:7][C@H:6]([CH3:48])[C:5](=[O:49])[NH:4][C@@H:3]1[CH:50]([CH3:52])[CH3:51]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86639580HCID 86639580, compound

Product 1

HCID 25152743HCID 25152743, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9 (8 mg, 0.011 mmol) in CH2Cl2 (1 mL) was added triethylsilane (7 μL, 0.44 mmol) was added dropwise TFA (0.2 mL, 20% v/v). After stirring for 1.5 h the reaction was concentrated in vacuo and purified by flash column chromatography (eluent 1:0-99:1-98:2-97:3-96.4 CH2Cl2/MeOH) to give the product 10 (0.47 mg, 0.001 mmol, 9%) as a white solid: Rf 0.44 MeOH/CH2Cl2 (1:9); MS (ES+) 584.2 (100%, [M+Na]+).

Workup

  1. concentrationwas concentrated in vacuo
  2. custompurified by flash column chromatography (eluent 1:0-99:1-98:2-97:3-96.4 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-c2a92956c3174fb18bb381fbd2907b9f
Source dataset
uspto-grants-2014_10
Patent number
US08865655B2

Reaction notes

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