Dichloromethane → [3-({tert-Butoxycarbonyl-[2-(2-hydroxy-phenyl)-ethyl]-amino}-methyl)-phenyl]-acetic acid methyl ester

HRID 553312

Reaktionsgleichung

Reaktionsgleichung von HRID 553312
Br.[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][NH2:7].[CH3:12][O:13][C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=O)[CH:17]=1.CN1[CH2:30][CH2:29][CH2:28]C1=O.[C:32]([O:35][BH-](OC(=O)C)OC(=O)C)(=[O:34])C.[Na+].Cl[CH2:47]Cl>>[CH3:12][O:13][C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:7]([C:32]([O:35][C:29]([CH3:28])([CH3:30])[CH3:47])=[O:34])[CH2:6][CH2:5][C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[OH:2])[CH:17]=1

Komponenten

6

Edukt 5

HCID 6344DichloromethaneHCID 13387N-methyl-2-pyrrolidoneHCID 5049666Sodium triacetoxyborohydrideHCID 11819590Methyl 2-(3-formylphenyl)acetateHCID 122805872-Hydroxyphenethylamine hydrobromide

Produkt 1

HCID 67166219[3-({tert-Butoxycarbonyl-[2-(2-hydroxy-phenyl)-ethyl]-amino}-methyl)-phenyl]-acetic acid methyl ester

Versuchsvorschrift

A mixture of 2-hydroxyphenethylamine hydrobromide salt (480 mg) and (3-formylphenyl)acetic acid methyl ester prepared as described in Example 1 (step a, 370 mg) in dichloromethane (10 mL) and 1-methyl-2-pyrrolidone (2 mL) was stirred for 30 minutes and then treated with sodium triacetoxyborohydride (1.02 g) The mixture was stirred for 18 hours and at the end of this time partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, the organic layer was separated, dried and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane (20 mL) and treated with di-tert-butyl-dicarbonate (480 mg). The solution was stirred for 5 hours, at the end of this time the solvent was removed under reduced pressure. The residue was purified on silica eluting with 20% ethyl acetate in isohexane to yield the sub-titled compound (560 mg).

Aufarbeitung

  1. customprepared
  2. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. customthe organic layer was separated
  4. customdried
  5. customthe solvent removed under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  7. additiontreated with di-tert-butyl-dicarbonate (480 mg)
  8. stirringThe solution was stirred for 5 hours, at the end of this time the solvent
  9. customwas removed under reduced pressure
  10. customThe residue was purified on silica eluting with 20% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-5be678a342334f5aa52711ac2e9717a3
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951954B2

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