Ammonia → 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester

HRID 581117

Reaktionsgleichung

Reaktionsgleichung von HRID 581117
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][O:8][C:9](=[O:30])[CH:10]([O:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([CH3:29])[N:17]2[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:11].[NH3:31]>CCOC(C)=O>[NH2:31][C:1](=[O:5])[C:2]([C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[CH:21][C:13]=2[O:12][CH:10]([CH3:11])[C:9]([O:8][CH3:7])=[O:30])[N:17]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:16]=1[CH3:29])=[O:3]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 106396522-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester

Produkt 1

HCID 105967932-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Oxalyl chloride (0.16 mL, 1.9 mmol) was reacted with 480 mg (1.5 mmol) of dl-2-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester and then reacted with anhydrous ammonia as in Example 1, Part F and the reaction product was dissolved in EtOAc, washed with water, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel (eluted with EtOAc) to give 531 mg (90% yield) of dl-2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid, methyl ester, melting at approximately 175° C.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (eluted with EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-da37ef5682ec4d4ca3a222758c0ad30f
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919810

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