Ethanol → (2R/S,4R)-methyl 2-(3,4-dihydroxyphenyl)thiazolidine-4-carboxylate

HRID 338804ノート

反応式

HRID 338804 の反応式
C(O)C.C([O-])(O)=O.[Na+].[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[OH:18])[CH:13]=O.Cl.[CH3:20][O:21][C:22](=[O:27])[C@H:23]([CH2:25][SH:26])[NH2:24]>O>[OH:9][C:10]1[CH:11]=[C:12]([CH:13]2[NH:24][C@H:23]([C:22]([O:21][CH3:20])=[O:27])[CH2:25][S:26]2)[CH:15]=[CH:16][C:17]=1[OH:18]

参加物

6

反応物 4

HCID 702EthanolHCID 87683,4-DihydroxybenzaldehydeHCID 516892Sodium BicarbonateHCID 2733208L-Cysteine, methyl ester, hydrochloride

生成物 1

HCID 60194724(2R/S,4R)-methyl 2-(3,4-dihydroxyphenyl)thiazolidine-4-carboxylate収率 83.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

In a co-solvent of ethanol (5 mL) and water (5 mL), a solution including NaHCO3 (486 mg, 5.79 mmol), 3,4-dihydroxybenzaldehyde (3,4-dihydroxybenzaldehyde) (800 mg, 5.80 mmol), and L-cysteine methyl ester hydrochloride (1.0 g, 5.84 mmol) was stirred at room temperature for 5 hours. After ethanol was evaporated, the reaction mixture was distributed between ethyl acetate and water, and an organic layer was dried, filtered, and evaporated. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (4:1) to obtain a solid Compound 104 (1.23 g, 83%).

後処理

  1. customAfter ethanol was evaporated
  2. customan organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-14f809b6639b4128a3d325841798e318
出典データセット
uspto-grants-2014_11
特許番号
US08889881B2

反応ノート

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