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

HRID 749221

反応式

HRID 749221 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5e9a18611874429e838a1a4755b0de8f
出典データセット
uspto-grants-2008_07
特許番号
US07402600B2

関連ノート

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