Dicyclohexylcarbodiimide → benzotriazol-1-yl (2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate

HRID 483024

Reaktionsgleichung

Reaktionsgleichung von HRID 483024
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH3:32])/[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[N:35]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH3:32])/[C:27]([O:29][N:34]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[N:36]=[N:35]2)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5928144(Z)-2-methoxymino-2-(2-(tritylamino)thiazol-4-yl)acetic acid

Produkt 1

HCID 88675991benzotriazol-1-yl (2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetic acid (2.22 g, 5 mmol) and 1-hydroxybenzotriazole (0.74 g, 5.5 mmol) in tetrahydrofuran (22 ml) was added N,N'-dicyclohexylcarbodiimide (1.14 g, 5.5 mmol) at 5°-10° C. and the mixture was stirred at the same temperature for 3 hours. Precipitated N,N'-dicyclohexylurea was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform (20 ml) and insoluble material was removed by filtration. The chloroform was evaporated and the residue was treated with a small quantity of ether to give colorless needles of 1-benzotriazolyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetate (2.60 g, 93%), mp 178°-179° C. (decomposition).

Aufarbeitung

  1. customPrecipitated N,N'-dicyclohexylurea was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform (20 ml)
  4. custominsoluble material was removed by filtration
  5. customThe chloroform was evaporated
  6. additionthe residue was treated with a small quantity of ether

Quellen und Nachweise

ORD-Eintrag
ord-de584faa82294b62aa037648a02c0640
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04576938

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