Triethylamine → HCID 85059266, compound

HRID 2222931Notes

Reaction equation

HRID 2222931 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH:11]2[C:17]([OH:19])=O)=[CH:4][CH:3]=1.C1CN([P+](O[N:37]2N=[N:44][C:39]3C=CC=C[C:38]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:38]([CH2:39][NH:44][C:17]([CH:11]1[CH2:12][CH:13]([CH3:16])[CH2:14][CH2:15][CH:10]1[CH2:9][S:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:19])#[N:37]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 69114680HCID 69114680, compound

Product 1

HCID 85059266HCID 85059266, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (1R/S,3R/S,6R/S)-2-{[(4-fluorophenyl)sulfanyl]methyl}-5-methylcyclohexanecarboxylic acid and (1R/S,3S/R,6R/S)-2-{[(4-fluorophenyl)sulfanyl]methyl}-5-methylcyclohexanecarboxylic acid (1:1 mixture, 52 mg, 0.18 mmol), PyBOP (144 mg, 0.28 mmol), and aminoacetonitrile hydrochloride (34 mg, 0.37 mmol) was added dry dimethylformamide (2 mL) under an atmosphere of dry nitrogen followed by triethylamine (103 μL, 0.74 mmol) and the reaction mixture was stirred for 5 h at room temperature. The reaction mixture was poured into aqueous saturated sodium hydrogen carbonate, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was concentrated in vacuo and the crude product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 30/70 to 50/50) to yield (1R/S,3R/S,6R/S)-N-(cyanomethyl)-2-{[(4-fluorophenyl)sulfanyl]-methyl}-5-methylcyclohexanecarboxamide and (1R/S,3S/R,6R/S)-N-(cyanomethyl)-2-{[(4-fluorophenyl)sulfanyl]methyl}-5-methylcyclohexanecarboxamide as a 1:1 mixture of diastereomers.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated in vacuo
  4. customthe crude product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 30/70 to 50/50)

Sources & evidence

ORD record
ord-fd1d5e8a19f040de84e1419b54064400
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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