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

HRID 391770

반응식

HRID 391770 반응식
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([OH:14])[CH:8]=1)[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[CH2:20]=O>O>[OH:14][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[OH:13])[CH2:20][NH:1][C@H:2]([C:3]([OH:5])=[O:4])[CH2:6]2

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 6047Levodopa

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

(S)-2-Amino-3-(3,4-dihydroxy-phenyl)-propionic acid (90 g) was suspended in 0.8 L water, then 18.2 mL concentrated sulfuric acid in 0.5 L additional water was added with stirring. Formaldehyde solution (136 mL, 37 wt %) was then added while stirring and the mixture was stirred 18 hours at rt. It was quenched by addition of 24.4 g NaOH in 0.5 L water, dropwise over 1 h while cooling. The resulting mixture was stored overnight at 4° C., and the solid that formed was collected by filtration, washed with hot water (70° C.), cooled again and collected by filtration. The solid was treated with 0.5 L MeOH and evaporated, then stored under vacuum overnight to give 65 g desired product. 1H NMR (400 MHz, MeOH-d4): 6.64 (s, 1H), 6.59 (s, 1H), 4.29-4.21 (m, 3H), 3.29-3.21 (m, 1H), 3.11-3.01 (m, 1H).

후처리

  1. stirringwhile stirring
  2. stirringthe mixture was stirred 18 hours at rt
  3. customIt was quenched by addition of 24.4 g NaOH in 0.5 L water, dropwise over 1 h
  4. temperaturewhile cooling
  5. customthe solid that formed
  6. filtrationwas collected by filtration
  7. washwashed with hot water (70° C.)
  8. temperaturecooled again
  9. filtrationcollected by filtration
  10. additionThe solid was treated with 0.5 L MeOH
  11. customevaporated
  12. customstored under vacuum overnight

출처 및 근거

ORD 기록
ord-82db86c22e6b4512ac5292b2e6a6a70b
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383644B2

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