Methanol → 1-Carbamoyl-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethane

HRID 987129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987129
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:29][CH2:30][CH3:31])[C:26](O)=[O:27])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.[N:39]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.ClCCl.CO>CN(C=O)C>[C:26]([CH:25]([O:29][CH2:30][CH3:31])[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:10][CH:11]=2)=[CH:19][CH:20]=1)(=[O:27])[NH2:39]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 6344DichloromethaneHCID 2724699PyBOPHCID 229884463-{4-[2-(4-tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid

Produkt 1

HCID 229884671-Carbamoyl-2-[4-(2-{4-tert-butyloxycarbonylaminophenyl}ethoxy)phenyl]-1-ethoxyethaneAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-{4-[2-(4-tert-Butoxycarbonylamino phenyl}ethoxy]phenyl]-2-ethoxypropanoic acid (1.18 g, 2.75 mmole) and benzotriazol-1-yl-oxytri-pyrrolidinophosphoniumhexafluorophosphate (1.43 g, 2.75 mmole) were dissolved in dry DMF (20 ml). Ammonia gas was bubbled through the mixture for 5 minutes. After stirring at room temperature for 16 hours it was checked using HPLC that all the starting material was consumed. Water was added and extracted three times with ethyl acetate dried with magnesium sulfate and evaporated. The residue was redissolved in dichloromethane and chromatography on silica using a gradient system of dichloromethane:methanol (0-5%) gave 1.04 g (85% yield) of the desired product.

Aufarbeitung

  1. customAmmonia gas was bubbled through the mixture for 5 minutes
  2. customwas consumed
  3. additionWater was added
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue was redissolved in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-2b7aefd4e38a42a0862be64f64aed055
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630509B2

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