2-Naphthyl isocyanate → 2-(3-(2-Chlorobenzyl)-1-methylureido)ethyl naphthalen-2-ylcarbamate

HRID 655974

Reaktionsgleichung

Reaktionsgleichung von HRID 655974
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][OH:11])[CH3:8].[N:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=[C:18]=[O:19]>C1COCC1.CN(C1C=CN=CC=1)C>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[NH:17][C:18](=[O:19])[O:11][CH2:10][CH2:9][N:7]([CH3:8])[C:6]([NH:5][CH2:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[Cl:1])=[O:12]

Komponenten

5

Edukt 2

HCID 167182-Naphthyl isocyanateHCID 597785693-(2-Chlorobenzyl)-1-(2-hydroxyethyl)-1-methylurea

Produkt 1

HCID 237291332-(3-(2-Chlorobenzyl)-1-methylureido)ethyl naphthalen-2-ylcarbamateAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(2-chlorobenzyl)-1-(2-hydroxyethyl)-1-methylurea (120 mg, 0.50 mmol) in THF (1.0 mL) were added DMAP (3.0 mg, 0.02) and 2-isocyanatonaphthalene (100 mg, 0.60 mmol). The reaction mixture was stirred for 30 min. LC/MS indicated the completion of the reaction. The mixture was filtered and the filtrate was purified by RP-HPLC using a mixture of acetonitrile and H2O to give 2-(3-(2-chlorobenzyl)-1-methylureido)ethyl naphthalen-2-ylcarbamate (165 mg, 80%). LRMS (M-Boc+H+) m/z 412.1.

Aufarbeitung

  1. customthe completion of the reaction
  2. filtrationThe mixture was filtered
  3. customthe filtrate was purified by RP-HPLC
  4. additiona mixture of acetonitrile and H2O

Quellen und Nachweise

ORD-Eintrag
ord-6c64a81e48a3483fa88e7aaf0ad60eb2
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071625B2

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