Triethylamine → HCID 178441311、化合物

HRID 1888683

反応式

HRID 1888683 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

HCID 178441311HCID 178441311、化合物収率 42%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ccf2d8a587934c3fb2a03827fc1a39bc
出典データセット
uspto-grants-2013_08
特許番号
US08501794B2

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