Hydrochloric Acid → (3S)-6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 478947

反応式

HRID 478947 の反応式
[CH:1]1[C:6]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:5][C:4]([OH:13])=[C:3]([OH:14])[CH:2]=1.Cl.O.[CH2:17]=O.[OH-].[Na+]>O>[OH:13][C:4]1[CH:5]=[C:6]2[C:1](=[CH:2][C:3]=1[OH:14])[CH2:17][NH:12][C@H:8]([C:9]([OH:11])=[O:10])[CH2:7]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6047LevodopaHCID 14798Sodium HydroxideHCID 22136924Formaldehyde--water (1/1)

生成物 1

HCID 12926159(3S)-6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid収率 95.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
2.5 °C

実験手順

To a cold (0-5° C.) suspension of Levodopa (197.2 g, 1.0 mol) in water (1.18 L) was added 32% aqueous HCl (159.5 g, 1.4 mol). The resulting solution was cooled to 0-5° C., and 37% formaldehyde water solution (243.24 g, 3.0 mol) was added. The resulting solution was allowed to warm to 20-25° C., and stirred at 20-25° C. for 10 h. The reaction solution was cooled to 0-5° C., and 2 N aqueous NaOH (700 mL, 1.4 mol) was slowly added to adjust pH to 5-5.5. White or light yellow solids precipitated during the addition. The resulting suspension was stirred at 0-5° C. for 2-3 h. The mixture was filtered, and rinsed with water (2×500 mL). The solids were dried under vacuum to give 199.52 g of a light yellow solid. Yield=95.3%.

後処理

  1. temperatureto warm to 20-25° C.
  2. temperatureThe reaction solution was cooled to 0-5° C.
  3. customWhite or light yellow solids precipitated during the addition
  4. stirringThe resulting suspension was stirred at 0-5° C. for 2-3 h
  5. filtrationThe mixture was filtered
  6. washrinsed with water (2×500 mL)
  7. customThe solids were dried under vacuum

出典と根拠

ORDレコード
ord-6ceb0d06cf6e43d39071939c1c56122e
出典データセット
uspto-grants-2003_11
特許番号
US06642384B1

関連ノート

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