Lithium hydroxide, monohydrate → (R)-3-(2-Chloro-N-methylphenylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1253660ノート

反応式

HRID 1253660 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([C@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24]C)=[O:23])[CH:20]=2)[CH2:15][CH2:14]1)[CH3:12])(=[O:10])=[O:9].O[Li].O>CO.C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([C@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([OH:24])=[O:23])[CH:20]=2)[CH2:15][CH2:14]1)[CH3:12])(=[O:9])=[O:10]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 59505532(R)-Methyl 3-(2-chloro-N-methylphenylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate

生成物 1

HCID 59505351(R)-3-(2-Chloro-N-methylphenylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylic acid収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a cooled (0° C.) solution of (R)-methyl 3-(2-chloro-N-methylphenylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (C-16) (840 mg, 2.216 mmol, 1.0 eq.) in MeOH:THF (1:1, 20 ml) was added dropwise a solution of LiOH.H2O (185 mg, 4.433 mmol, 2.0 eq.) in water (10 ml) and the reaction mixture was stirred at RT for 3 h. After completion of the reaction (monitored by TLC), the reaction mixture was concentrated to dryness and diluted with water (20 ml) and washed with ethyl acetate (20 ml). The aqueous layer was acidified to pH≈3 using 1N HCl and then extracted with methylene chloride (2×50 ml). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to afford the desired product as an off-white solid. Yield: 58% (470 mg, 1.2876 mmol).

後処理

  1. customAfter completion of the reaction (monitored by TLC)
  2. concentrationthe reaction mixture was concentrated to dryness
  3. additiondiluted with water (20 ml)
  4. washwashed with ethyl acetate (20 ml)
  5. extractionextracted with methylene chloride (2×50 ml)
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-a81f7a5d3b0b4106a6eee065232d9c11
出典データセット
uspto-grants-2013_06
特許番号
US08455475B2

反応ノート

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