Trifluoroacetic acid → HCID 46892695, compound

HRID 1425632Notes

Reaction equation

HRID 1425632 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]([C:20]3[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=3)C(=O)OC(C)(C)C)=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:28][N:29]([C:37]1[CH:42]=[C:41]([CH3:43])[CH:40]=[C:39]([CH3:44])[N:38]=1)C(=O)OC(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][NH:12][C:20]3[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:28][NH:29][C:37]1[CH:42]=[C:41]([CH3:43])[CH:40]=[C:39]([CH3:44])[N:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 52936386HCID 52936386, compound

Product 1

HCID 46892695HCID 46892695, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6a (590 mg, 1.0 mmol) in CH2Cl2 (8 mL) was added trifluoroacetic acid (TFA, 8 mL). The reaction mixture was allowed to stir at room temperature for 8 h then was concentrated. The crude product was purified by flash column chromatography (2-5% MeOH in CH2Cl2) to yield 3a (355 mg, 90%) as a white solid: 1H NMR (500 MHz, CD3OD/CDCl3) δ 2.28 (s, 6H), 2.48 (s, 6H), 4.60 (s, 4H), 6.46 (s, 4H), 7.45-7.47 (d, J=8.5, 2H), 7.78 (s, 2H), 7.84-7.86 (d, J=8.5, 2H); 13C NMR (125 MHz, CD3OD/CDCl3) δ 18.6, 22.0, 45.9, 106.8, 114.5, 125.6, 129.0, 133.1, 134.3, 147.6, 153.8, 158.0; ESI (M+H+) calcd for C26H29N4 397.23922, found 397.23999.

Workup

  1. concentrationthen was concentrated
  2. customThe crude product was purified by flash column chromatography (2-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-030741cd555b473faa85b3618aa41644
Source dataset
uspto-grants-2015_01
Patent number
US08932842B2

Reaction notes

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