Ethyl Acetate → 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

HRID 1904468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1904468
[Cl-].[C:2]1([N+:8]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=CC=CC2C(=O)N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23]1([CH2:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH2:41][CH3:42])[CH:36]=[C:35]3[CH2:43][C:44]2[CH:52]=[CH:51][C:47]([C:48]([OH:50])=[O:49])=[CH:46][C:45]=2[O:53][CH3:54])=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.[OH-].[Na+].C(OCC)(=[O:59])C>CO.CN(C)C=O>[C:17]1([N:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13]([O:49][C:48](=[O:50])[C:47]2[CH:51]=[CH:52][C:44]([CH2:43][C:35]3[C:34]4[C:38](=[CH:39][CH:40]=[C:32]([NH:31][C:29](=[O:30])[CH2:28][CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[CH:33]=4)[N:37]([CH2:41][CH3:42])[CH:36]=3)=[C:45]([O:53][CH3:54])[CH:46]=2)=[O:59])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 146268494-[5-(2-Cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic acidHCID 86743117N,N-diphenylcarbamoylpyridinium chloride

Produkt 1

HCID 867431194-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N,N-diphenylcarbamoylpyridinium chloride (311 mg) in methanol (1 ml) was added to a stirred solution of the acid (J) (450 mg) and sodium hydroxide (1 ml of a 1M aqueous solution) in methanol (4 ml) under an atmosphere of nitrogen. After stirring for 1.5 minutes, ethyl acetate and N,N-dimethylformamide (2 ml) were added and the mixture allowed to stir until all dissolved. The ethyl acetate solution was washed with water and saturated brine, dried (MgSO4) and evaporated to give a quantitative yield of 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride (E) as a crusty foam; partial NMR: (80 MHz, DMSO-d6): 1.30(t, J=7.1 Hz, 2H, NCH2CH3), 3.84(s, 3H, OCH3), 3.94(s, 2H, ArCH2), 4.05(q, J=7.1 Hz, 2H, NCH2CH3), 7.41(s, 10H, NArH), 9.56(s, 1H, CONH).

Aufarbeitung

  1. stirringto stir until all dissolved
  2. washThe ethyl acetate solution was washed with water and saturated brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1d1426579a924c6e9b608c04d3fd6f32
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04837235

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