Water → (2R)-3-methyl-2-(naphthalen-2-ylsulfonylamino)butanoic acid

HRID 265612

反応式

HRID 265612 の反応式
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].O.C(N(CC)CC)C.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[S:27](Cl)(=[O:29])=[O:28]>C1COCC1>[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[S:27]([NH:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:28])=[O:29]

参加物

6

反応物 4

HCID 962WaterHCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 71563D-Valine

生成物 1

HCID 730260(2R)-3-methyl-2-(naphthalen-2-ylsulfonylamino)butanoic acid収率 87%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a 12-L 3-neck flask with a mechanical stirrer, an addition funnel, and a thermometer were added 400 g (3.414 mol) of D-valine (36.0), 3 L of water, 380 mL of THF, and 1190 mL (8.572 mol) of triethylamine (TEA). To this solution was added dropwise at 5°-10° C. a solution of 774 g (3.414 mol) of 2-naphthalenesulfonyi chloride (35.0) in 800 mL THF. The mixture was allowed to warm to room temperature and stirred for 2 hours. Evaporation of THF followed by quenching into 4 L of 3 N HCl precipitated crude product. Crystallization of the crude product from t-butyl methyl ether gave 910 g (87%) of 18.1. M.p: 170°-172° C. (literature gives the m.p. as 170°-172° C.-see Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem., 1991, 56, 2276.). The spectrum data are identical to that of the literature.

後処理

  1. customEvaporation of THF
  2. customby quenching into 4 L of 3 N HCl
  3. customprecipitated crude product
  4. customCrystallization of the crude product from t-butyl methyl ether

出典と根拠

ORDレコード
ord-a02c0bc24d1d466785340419b0601f27
出典データセット
uspto-grants-1997_07
特許番号
US05648484

関連ノート

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