Trifluoroacetic acid → HCID 53330343, compound

HRID 39310Notes

Reaction equation

HRID 39310 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:39])[N:15]([C:25]2[CH:29]=[C:28]([C:30]#[C:31][C:32]([CH3:35])([CH3:34])[CH3:33])[S:27][C:26]=2[C:36]([OH:38])=[O:37])[C:16]([CH:18]2[CH2:23][CH2:22][CH:21]([CH3:24])[CH2:20][CH2:19]2)=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[CH3:33][C:32]([CH3:34])([CH3:35])[C:31]#[C:30][C:28]1[S:27][C:26]([C:36]([OH:38])=[O:37])=[C:25]([N:15]([C:16]([CH:18]2[CH2:19][CH2:20][CH:21]([CH3:24])[CH2:22][CH2:23]2)=[O:17])[N:14]([CH3:39])[CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53328177HCID 53328177, compound

Product 1

HCID 53330343HCID 53330343, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Crude 4-[N′-[2-carboxy-5-(3,3-dimethyl-but-1-ynyl)-thiophen-3-yl]-N-methyl-N′-(4-methyl-cyclohexanecarbonyl)-hydrazino]-piperidine-1-carboxylic acid tert-butyl ester (220 mg, 500 mmol) (Example 127) was treated with TFA (3 mL, 4.6 mmol) at 60° C. for 10 min. After cooling, toluene (2-3 mL) was added and the mixture was concentrated, this was repeated several times, and a portion of this crude material was purified by HPLC (Gemini column, 35% acetonitrile:water, 2 min, 35-50% acetonitrile:water, 2 min, 50-95% acetonitrile: water 13 min, both solvents containing 0.1% trifluoroacetic acid). This resulted in 20 mg of the title compound as a white powder (bis-TFA salt): MS (m/z): 460.2 [M−H]+; HPLC retention time: 3.15 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. customa portion of this crude material was purified by HPLC (Gemini column, 35% acetonitrile
  4. additionwater, 2 min, 35-50% acetonitrile:water, 2 min, 50-95% acetonitrile: water 13 min, both solvents containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-294272d9ddbf4ed1b8a43c6b703ec856
Source dataset
uspto-grants-2013_09
Patent number
US08524764B2

Reaction notes

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