Hydrochloric Acid → HCID 66865340, 화합물

HRID 251878

반응식

HRID 251878 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 66865340HCID 66865340, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-51121f69f34f49c8801569dca446b58d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868003B2

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