Hydrochloric Acid → 3-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-1-methylimidazolidine-2,4-dione hydrochloride

HRID 251878

反応式

HRID 251878 の反応式
[N+](C1C=CC([N:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C@H:20]2[C:29]3[C:24](=[C:25]([Cl:31])[CH:26]=[C:27]([Cl:30])[CH:28]=3)[CH2:23][N:22]([CH3:32])[CH2:21]2)[C:11](=O)[O-:12])=CC=1)([O-])=O.Cl.CO[C:36](=[O:40])[CH2:37][NH:38][CH3:39].C(N(CC)CC)C.Cl>C1COCC1.O>[ClH:30].[Cl:30][C:27]1[CH:28]=[C:29]2[C:24](=[C:25]([Cl:31])[CH:26]=1)[CH2:23][N:22]([CH3:32])[CH2:21][C@H:20]2[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:10]1[C:36](=[O:40])[CH2:37][N:38]([CH3:39])[C:11]1=[O:12]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 66864077HCID 66864077、化合物

生成物 1

HCID 668653403-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-1-methylimidazolidine-2,4-dione hydrochloride

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

4-Nitrophenyl[2-((R)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]carbamate (125 mg) was dissolved in absolute THF (5 ml), and sarcosine methyl ester hydrochloride and triethylamine were added dropwise with stirring. After stirring for 5 h, the reaction mixture was freed of the solvent, and the residue was admixed with water and 2 N hydrochloric acid and refluxed for 2 h. After standing overnight, the reaction mixture was concentrated and admixed with ethyl acetate, water and saturated potassium carbonate solution. After separation of the phases, the organic phase was washed five times with saturated potassium carbonate solution and twice with saturated sodium chloride solution. Drying over magnesium sulfate and filtration were followed by concentration. The residue was purified by means of preparative HPLC. The fractions comprising product were combined, the acetonitrile was removed on a rotary evaporator, and the aqueous residue was neutralized with saturated potassium carbonate solution and extracted three times with ethyl acetate. After the combined ethyl acetate phases had been dried over magnesium sulfate, they were filtered and concentrated to dryness. The residue was taken up with water/hydrochloric acid and freeze-dried. 60 mg of the title compound were obtained.

後処理

  1. stirringAfter stirring for 5 h
  2. temperaturerefluxed for 2 h
  3. concentrationthe reaction mixture was concentrated
  4. customAfter separation of the phases
  5. washthe organic phase was washed five times with saturated potassium carbonate solution
  6. dry with materialDrying over magnesium sulfate and filtration
  7. concentrationwere followed by concentration
  8. customThe residue was purified by means of preparative HPLC
  9. customthe acetonitrile was removed on a rotary evaporator
  10. extractionextracted three times with ethyl acetate
  11. dry with materialAfter the combined ethyl acetate phases had been dried over magnesium sulfate, they
  12. filtrationwere filtered
  13. concentrationconcentrated to dryness
  14. customfreeze-dried

出典と根拠

ORDレコード
ord-51121f69f34f49c8801569dca446b58d
出典データセット
uspto-grants-2011_01
特許番号
US07868003B2

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