HCID 71003871, compound → HCID 70974539, compound

HRID 1424564Notes

Reaction equation

HRID 1424564 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([NH:23][C:24](=[O:46])[C@@H:25]([NH:38]C(=O)OC(C)(C)C)[CH2:26][CH2:27][CH2:28][CH2:29][NH:30]C(=O)OC(C)(C)C)[CH:12]=[C:13]([C:15]#[C:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O>[NH2:38][C@@H:25]([CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[C:24]([NH:23][C:11]1[CH:10]=[C:9]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=[C:13]([C:15]#[C:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=1)=[O:46]

Participants

3

Reactant 1

HCID 71003871HCID 71003871, compound

Product 1

HCID 70974539HCID 70974539, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-di-tert-butyl (6-((3,5-bis(phenylethynyl) phenyl)amino)-6-oxohexane-1,5-diyl)dicarbamate (0.35 g, 0.56 mmol) was reacted with neat TFA (10 mL) and the solution was stirred for 5 hours at room temperature. TFA was evaporated and the product (0.34 mg, 93%) was purified by recrystallization with ethanol: 1H-NMR (400 MHz, CD3OD) δ 7.80 (d, J=1.4 Hz, 2H), 7.52-7.55 (m, 4H), 7.45 (t, J=1.4 Hz, 1H), 7.38-7.41 (m, 6H), 4.06 (t, J=6.5 Hz, 1H), 2.96 (t, J=15.4 Hz, 2H), 1.96-2.06 (m, 2H), 1.70-1.78 (m, 2H), 1.50-1.60 (m, 2H).

Workup

  1. customTFA was evaporated
  2. customthe product (0.34 mg, 93%) was purified by recrystallization with ethanol

Sources & evidence

ORD record
ord-6c22b8e5ec5941c29ce17102cea6b7ff
Source dataset
uspto-grants-2015_01
Patent number
US08927728B2

Reaction notes

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