N,N-Diethylethanamine trihydrofluoride → HCID 178442389, compound

HRID 1886993Notes

Reaction equation

HRID 1886993 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([C:24]([C@H:26]1[CH2:31][CH2:30][C@H:29]([CH3:32])[CH2:28][CH2:27]1)=[O:25])[C:10]1[CH:14]=[C:13]([C:15]#[C:16][C:17]([CH3:20])([CH3:19])[CH3:18])[S:12][C:11]=1[C:21]([OH:23])=[O:22])(C)(C)C.CCN(CC)CC.F.F.F>C1COCC1>[CH3:19][C:17]([CH3:18])([CH3:20])[C:16]#[C:15][C:13]1[S:12][C:11]([C:21]([OH:23])=[O:22])=[C:10]([N:9]([CH2:8][CH2:7][OH:6])[C:24]([C@H:26]2[CH2:31][CH2:30][C@H:29]([CH3:32])[CH2:28][CH2:27]2)=[O:25])[CH:14]=1

Participants

4

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 178442390HCID 178442390, compound

Product 1

HCID 178442389HCID 178442389, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid (273 mg) in THF (4 mL) was treated with triethylaminetrihydrofluoride (0.5 mL). After 1 hour, volatiles were removed under vacuum and the residue was purified by silica gel chromatography (0-10% Methanol:DCM) to provide 83 mg of 5-(3,3-Dimethyl-but-1-ynyl)-3-[(2-hydroxy-ethyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid.

Workup

  1. customvolatiles were removed under vacuum
  2. customthe residue was purified by silica gel chromatography (0-10% Methanol:DCM)

Sources & evidence

ORD record
ord-59af2df121154a798096ec9f1c6abd49
Source dataset
uspto-grants-2013_08
Patent number
US08501714B2

Reaction notes

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