Hydrochloric Acid → HCID 58248298, 화합물

HRID 388860노트

반응식

HRID 388860 반응식
[O:1]=[C:2]1[N:10](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:32][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([CH:30]=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2.Cl.OS(O)(=O)=O.[OH-].[Na+]>CO.O>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:32][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([CH:30]=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric Acid2회HCID 14798Sodium HydroxideHCID 58550623HCID 58550623, 화합물

생성물 1

HCID 58248298HCID 58248298, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

To a solution of (2S)-2′-oxo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,1′,2′,3-tetrahydrospiro[cyclopenta[b]quinoline-2,3′-pyrrolo[2,3-b]pyridine]-7-carbaldehyde from Step I (142 mg, 0.320 mmol) in MeOH (17 mL) was introduced gaseous anhydrous hydrogen chloride by bubbling the gas through the solution until the MeOH was saturated and mildly warmed. This saturation with HCl was repeated once again after 3 hours then the sealed reaction was allowed to sit at ambient temperature for 19 hours. The solution was then purged with a stream of nitrogen for 20-30 minutes, before being concentrated in vacuo. MeOH (50 mL) was added, then removed in vacuo, repeating this addition/concentration twice to remove excess HCl. The residue was dissolved in MeOH (17 mL) prior to the addition of concentrated aqueous NH4OH (0.7 mL). After 20 minutes the MeOH was removed in vacuo, fresh MeOH (50 mL) was added then remove in vacuo to produce a residue. This residue was dissolved in water (1.35 mL) plus 4 drops on cone. H2SO4. This aqueous solution was transferred to an Erlenmeyer flask using water (3 mL) and 2 more drops of conc. H2SO4. Slow neutralization with aqueous NaOH (1 M, ˜2.5 mL) provided a solid which was filtered, washed with water, air dried and vacuum dried to give the title compound. MS: m/z=316 (M+1).

후처리

  1. customby bubbling the gas through the solution until the MeOH
  2. temperaturemildly warmed
  3. customthe sealed reaction
  4. waitto sit at ambient temperature for 19 hours
  5. customThe solution was then purged with a stream of nitrogen for 20-30 minutes
  6. concentrationbefore being concentrated in vacuo
  7. additionMeOH (50 mL) was added
  8. customremoved in vacuo
  9. concentrationthis addition/concentration twice
  10. customto remove excess HCl
  11. dissolutionThe residue was dissolved in MeOH (17 mL)
  12. additionto the addition of concentrated aqueous NH4OH (0.7 mL)
  13. customAfter 20 minutes the MeOH was removed in vacuo, fresh MeOH (50 mL)
  14. additionwas added
  15. customthen remove in vacuo
  16. customto produce a residue
  17. customprovided a solid which
  18. filtrationwas filtered
  19. washwashed with water, air
  20. customdried
  21. customvacuum dried

출처 및 근거

ORD 기록
ord-f44a3adcacd349379965a8e271e5a167
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377955B2

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