Triethylamine → HCID 178441311, compound

HRID 1888683

Reaction equation

HRID 1888683 reaction equation
[C:1]([OH:14])(=[O:13])[C:2]1([CH2:12][CH2:11][CH:7]([C:8]([OH:10])=O)[C:4]1([CH3:6])[CH3:5])[CH3:3].P(Cl)(Cl)(Cl)(Cl)Cl.[C:21]([N:25]1[CH:29]=[C:28]([CH2:30][CH2:31][CH2:32][CH3:33])[C:27](=[NH:34])[S:26]1)([CH3:24])([CH3:23])[CH3:22].[CH2:35](N(CC)CC)C>CCCCCC.O1CCCC1.C(OC(=O)C)C.CO>[CH2:30]([C:28]1=[CH:29][N:25]([C:21]([CH3:24])([CH3:23])[CH3:22])[S:26]/[C:27]/1=[N:34]\[C:8]([C@H:7]1[CH2:11][CH2:12][C@@:2]([CH3:3])([C:1]([O:14][CH3:35])=[O:13])[C:4]1([CH3:5])[CH3:6])=[O:10])[CH2:31][CH2:32][CH3:33]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 214911,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acidHCID 24819Phosphorus pentachlorideHCID 668672282-tert-Butyl-4-butylisothiazol-5(2H)-imine

Product 1

HCID 178441311HCID 178441311, compoundYield 42%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (+)-camphoric acid (Aldrich, 2.00 g, 10.0 mmol) and phosphorus pentachloride (Aldrich, 4.16 g, 20.0 mmol) in hexane (75 mL) was heated to reflux and stirred for 24 hours. After cooling to ambient temperature, the reaction mixture was concentrated by rotary evaporator to give a pale yellow oil. The crude bis acid chloride (474 mg, 2.00 mmol) was added to a mixture of the product from Example 92B (425 mg, 2.00 mmol) and triethylamine (1.01 g, 10.0 mmol) in anhydrous tetrahydrofuran (12 mL). The mixture was stirred for 2 hours Anhydrous methanol (10 mL) was added and the resulting mixture was stirred overnight. The mixture was concentrated by rotary evaporator to give a brown oil. Flash chromatography (silica gel, 5-25% ethylacetate in hexanes) afforded 343 mg (42%) of the title compound. 1H NMR (DMSO-d6) δ 0.53 (s, 3H), 0.90 (t, J=7.3 Hz, 3H), 1.20 (s, 3H), 1.23 (s, 3H), 1.23-1.40 (m, 2H), 1.41-1.50 (m, 1H), 1.57 (s, 9H), 1.57-1.67 (m, 2H), 1.71-1.84 (m, 1H), 2.24-2.36 (m, 1H), 2.41-2.48 (m, 1H), 2.61-2.67 (m, 2H), 3.00-3.06 (m, 1H), 3.59 (s, 3H), 8.52 (s, 1H). MS (ESI+) m/z 409 (M+H)+. Anal. calcd. for C22H36N2O3S: C, 64.67; H, 8.88; N, 6.86. Found: C, 64.52; H, 8.76; N, 6.84.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. concentrationthe reaction mixture was concentrated by rotary evaporator
  4. customto give a pale yellow oil
  5. additionwas added
  6. stirringthe resulting mixture was stirred overnight
  7. concentrationThe mixture was concentrated by rotary evaporator
  8. customto give a brown oil

Sources & evidence

ORD record
ord-ccf2d8a587934c3fb2a03827fc1a39bc
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Linked notes

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