Triethylamine → HCID 178441311, 화합물

HRID 1888683

반응식

HRID 1888683 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

HCID 178441311HCID 178441311, 화합물수율 42%

시약·촉매·용매 4

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ccf2d8a587934c3fb2a03827fc1a39bc
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501794B2

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