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Carbon Dioxide → (S)-3-tert-butoxycarbonylamino-5-methyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carboxylic acid cyclopropylmethyl ester

HRID 1372971
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1372971
[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:22](=[O:24])=[O:23].Br[CH2:26][CH:27]1[CH2:29][CH2:28]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH:27]1([CH2:26][O:23][C:22]([N:10]2[CH2:9][C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:21])[C:14](=[O:15])[N:13]([CH3:16])[C:12]3[CH:17]=[CH:18][CH:19]=[CH:20][C:11]2=3)=[O:24])[CH2:29][CH2:28]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 280Carbon DioxideHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 57617767(S)-tert-Butyl (1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)carbamate

Produkt 1

HCID 69042563(S)-3-tert-butoxycarbonylamino-5-methyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carboxylic acid cyclopropylmethyl ester
Ausbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 350 mg (1.2 mmol) of (S)-(1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester [Example 103a] in 10 ml of N,N-dimethylformamide was treated successively with about 1 g of solid carbon dioxide, 237 mg (1.7 mmol) of bromomethyl-cyclopropane, and 626 mg (1.9 mmol) of cesium carbonate. The reaction mixture was stirred in a sealed flask at 80° C. during the weekend. For the working-up, the solvent was evaporated under reduced pressure and the residue was dissolved in a mixture of 30 ml of ethyl acetate and 10 ml of water. The organic layer was separated, dried over sodium sulphate and evaporated under reduced pressure. For the purification, the crude compound was chromatographed on silica gel using a 3:1-mixture of heptane and ethyl acetate as the eluent. There were obtained 410 mg (87% of theory) of the (S)-3-tert-butoxycarbonylamino-5-methyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carboxylic acid cyclopropylmethyl ester as a white gum;

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of 30 ml of ethyl acetate and 10 ml of water
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customFor the purification
  7. customthe crude compound was chromatographed on silica gel using a 3

Quellen und Nachweise

ORD-Eintrag
ord-9375fdd5c70b49acb2708b6844292249
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07160875B2

Notizen zur Reaktion

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