Sodium Carbonate → (R)-methyl 1-(methoxyamino)-1-oxo-3-phenylpropan-2-ylcarbamate

HRID 1530766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530766
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9]([NH:11][C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=O)=[O:10].Cl.[O:24]([NH2:26])[CH3:25].Cl.CN(C)CCCN=C=NCC>O.C(Cl)Cl.O1CCCC1>[CH3:25][O:24][NH:26][C:13](=[O:15])[C@H:12]([NH:11][C:9]([O:8][CH3:7])=[O:10])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10799103(R)-2-(methoxycarbonylamino)-3-phenylpropanoic acid

Produkt 1

HCID 10682227(R)-methyl 1-(methoxyamino)-1-oxo-3-phenylpropan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of sodium carbonate (10.20 g, 96.2 mmol) in water (170 ml) is added to a mixture of (R)-2-(methoxycarbonylamino)-3-phenylpropanoic acid (II, EXAMPLE 1, ˜0.148 mol crude) in methylene chloride. Methoxylamine hydrochloride (14.2 g, 0.170 mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (31.21 g, 0.163 mol) are added, and the mixture is stirred at 20-25° for 22 hours. The mixture is diluted with tetrahydrofuran (to dissolve the precipitate) and the layers are separated. The aqueous layer is extracted with 1:1 tetrahydrofuran/ether, and the combined organic extracts are washed with hydrochloric acid (10%) and saturated sodium bicarbonate solution. The mixture is dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. Crystallization from ethyl acetate gives the title compound, mp=154-155°; NMR (CDCl3) 3.05, 3.58, 3.61, 4.34, 5.66, 7.15-7.31 and 9.44 δ; IR (mineral oil) 1694 and 1668 cm−1; [a]25D=+5.2° (CH3OH, c=1.045).

Aufarbeitung

  1. dissolutionto dissolve the precipitate) and the layers
  2. customare separated
  3. extractionThe aqueous layer is extracted with 1:1 tetrahydrofuran/ether
  4. washthe combined organic extracts are washed with hydrochloric acid (10%) and saturated sodium bicarbonate solution
  5. dry with materialThe mixture is dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customCrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2c6e66cc773b45f2b8381506c676008a
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06197339B1

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