2-(6-Methoxy-2-naphthyl)propionic acid → 3-(6-methoxy-alpha-methyl-2-naphthalenacetyl)(R)-2-oxothiazolidin-4-carboxylic acid

HRID 749221

반응식

HRID 749221 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:17])[C:14]([OH:16])=O)[CH:7]=[CH:6]2.C(Cl)(=O)C(Cl)=O.[O:24]=[C:25]1[NH:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27][S:26]1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O.CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:17])[C:14]([N:29]1[C@H:28]([C:30]([OH:32])=[O:31])[CH2:27][S:26][C:25]1=[O:24])=[O:16])[CH:7]=[CH:6]2

참가 물질

9

반응물 4

HCID 13022-(6-Methoxy-2-naphthyl)propionic acidHCID 8471TriethylamineHCID 652722-Oxo-1,3-thiazolidine-4-carboxylic acidHCID 65578Oxalyl chloride

생성물 1

HCID 866029743-(6-methoxy-alpha-methyl-2-naphthalenacetyl)(R)-2-oxothiazolidin-4-carboxylic acid수율 68.5%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

To a solution of 6-methoxy-α-methyl-2-naphthalenacetic acid (7.0 g, 30.4 mmoles) in toluene (100 ml) and N,N-dimethylformamide (10 ml) cooled at 0° C., oxalylchloride (5.23 ml, 61 mmoles) is added. After 2 hours at room temperature the solution is evaporated at reduced pressure. To the solution of the obtained residue dissolved in tetrahydrofuran (50 ml) a mixture is added consisting of 2-oxothiazolidin-4-carboxylic acid (4.07 g, 27.6 mmoles), 4-dimethylaminopyridine (0.84 g, 6.9 mmoles), triethylamine (7.69 ml, 55.2 mmoles) in tetrahydrofuran (50 ml) cooled at −10° C. The mixture is left at room temperature for 24 hours. The reaction mixture is washed with HCl 5%, then with water. The organic phase is anhydrified with sodium sulphate and then evaporated at reduced pressure. The obtained residue is purified by chromatography on silica gel eluting with methylene chloride/methanol 95/5. 6.79 g of the expected product are obtained in the form of an amorphous solid.

후처리

  1. customAfter 2 hours at room temperature the solution is evaporated at reduced pressure
  2. dissolutionTo the solution of the obtained residue dissolved in tetrahydrofuran (50 ml) a mixture
  3. additionis added
  4. washThe reaction mixture is washed with HCl 5%
  5. customevaporated at reduced pressure
  6. customThe obtained residue is purified by chromatography on silica gel eluting with methylene chloride/methanol 95/5

출처 및 근거

ORD 기록
ord-5e9a18611874429e838a1a4755b0de8f
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402600B2

연결된 노트

불러오는 중…