Trifluoroacetic acid → HCID 86680183, compound

HRID 1184929Notes

Reaction equation

HRID 1184929 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:42]=[CH:43][CH:44]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19](=[O:41])[CH2:20][S:21]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:42]=[CH:43][CH:44]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19](=[O:41])[CH2:20][SH:21])[CH:13]=1)=[O:10])([CH3:4])[CH3:5])#[N:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67125572HCID 67125572, compound

Product 1

HCID 86680183HCID 86680183, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-cyanopropan-2-yl)-N-(4-methyl-3-(2-(tritylthio)acetyl)phenyl)benzamide 114 (0.799 mmol, 475 mg), trifluoroacetic acid (40.4 mmol, 3 mL) and triethylsilane (0.799 mmol, 0.129 mL) in CH2Cl2 (10 mL) was stirred 1 h at room temperature. Evaporated to dryness and purified by chromatography (10% ethyl acetate in CH2Cl2) gave 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetyl)-4-methylphenyl)benzamide 115 (71 mg, 25%). NMR (400 MHz, CDCl3) 1.79 (s, 6H), 2.51 (s, 3H), 3.93 (d, J=7.4 Hz, 2H), 7.30 (d, J=8.2 Hz, 1H), 7.54 (m, 2H), 7.72 (dq, J=7.8 Hz and 1.2 Hz, 1H), 7.80 (dt, J=7.8 Hz and 1.6 Hz, 1H), 7.90 (br s, 1H), 8.00 (t, J=2.0 Hz, 1H), 8.19 (d, J=2.0 Hz, 1H).

Workup

  1. customEvaporated to dryness
  2. custompurified by chromatography (10% ethyl acetate in CH2Cl2)

Sources & evidence

ORD record
ord-5af87a40ca7045e19d682721c6b1e2c3
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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