Phosgene → 2-(1-Tert-butoxycarbonyl-indol-3-yl)-2-oxo-ethylisocyanate

HRID 583783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583783
[NH2:1][CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=1)=[O:4].[H-].[Na+].Cl.NC[C:26](C1C2C(=CC=CC=2)N(C(OC(C)(C)C)=O)C=1)=[O:27].C(Cl)(Cl)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(OCC)(=O)C.C(OCC)C.ClCCl.N1C=CC=CC=1>[C:17]([O:16][C:14]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:3](=[O:4])[CH2:2][N:1]=[C:26]=[O:27])=[CH:6]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Komponenten

10

Edukt 5

HCID 6371PhosgeneHCID 24758Sodium hydrideHCID 94429TriphosgeneHCID 223425193-Aminoacetyl-1-(tert-butoxycarbonyl)-indole hydrochlorideHCID 223425203-Aminoacetyl-1-(tert-butoxycarbonyl)-indole

Produkt 1

HCID 223425462-(1-Tert-butoxycarbonyl-indol-3-yl)-2-oxo-ethylisocyanate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 3-aminoacetyl-1-(tert-butoxycarbonyl)-indole, which may be prepared as described in Step (e) above, (0.01 mol), optionally in the presence of from 1 to 3 mol equivalents of a volatile (i.e., boiling point <150° C.) non-nucleophilic base such as, for example, a volatile tertiary organic amine or pyridine, or a solid non-nucleophilic base such as, for example, sodium hydride, or 3-aminoacetyl-1-(tert-butoxycarbonyl)-indole hydrochloride, which may be prepared as described in Step (e) above, (0.01 mol), optionally in the presence of from 2 to 4 mol equivalents of said non-nucleophilic bases, in a solvent such as dichloromethane or ethyl acetate, is stirred. A suitable reagent such as, for example, 1 mol equivalent of phosgene or 0.33 mol equivalents of triphosgene is added. After stirring for from 10 minutes to about 24 hours, the mixture is diluted with up to an equal volume of a diluent such as diethyl ether or ethyl acetate (preferred diluent is diethyl ether), and any precipitates are filtered off. The filter cake is washed with additional diluent. The filtrate and washings are combined and rotary evaporated to give 2-(1-tert-butoxycarbonyl-indol-3-yl)-2-oxo-ethylisocyanate, which may be purified, if needed or desired, by vacuum distillation.

Aufarbeitung

  1. stirringAfter stirring for from 10 minutes to about 24 hours
  2. filtrationany precipitates are filtered off
  3. washThe filter cake is washed with additional diluent
  4. customrotary evaporated

Quellen und Nachweise

ORD-Eintrag
ord-cdbb0a7a9ba147afa9f6d95ebbdf9424
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924276B2

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