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Sodium Carbonate → Methyl [(3S)-5-(4-chlorophenyl)-7-(methyloxy)-2-thioxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]acetate

HRID 570164
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 570164
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].C([O-])([O-])=O.[Na+].[Na+].[CH3:21][O:22][C:23](=[O:46])[CH2:24][C@@H:25]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[C:29]2[CH:39]=[C:40]([O:43][CH3:44])[CH:41]=[CH:42][C:28]=2[NH:27][C:26]1=O>ClCCCl>[CH3:21][O:22][C:23](=[O:46])[CH2:24][C@@H:25]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[C:29]2[CH:39]=[C:40]([O:43][CH3:44])[CH:41]=[CH:42][C:28]=2[NH:27][C:26]1=[S:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 14817Phosphorus sulfide (P2S5)HCID 53261361(S)-methyl 2-(5-(4-chlorophenyl)-7-methoxy-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)acetate

Produkt 1

HCID 57465560Methyl [(3S)-5-(4-chlorophenyl)-7-(methyloxy)-2-thioxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11
1,2-Dichloroethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A suspension of P4S10 (85.8 g, 190 mmol) and Na2CO3 (20.5 g, 190 mmol) in 1,2-DCE (1.5 L) at RT was stirred for 1 h before methyl[(3S)-5-(4-chlorophenyl)-7-(methyloxy)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]acetate (for a preparation see Intermediate 5) (40 g, 107 mmol) was added. The resulting mixture was stirred at 65° C. for 4 h before being cooled and filtered. The solid was washed with DCM and the filtrate washed with sat. NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The title compound was precipitated from a DCM/i-Pr2O mixture and filtered. The filtrate was then concentrated and purified by flash chromatography (DCM/MeOH: 98/2) to afford another batch of product. The title compound was obtained combining the two fractions (30.2 g, 73%) as a yellow powder. LC/MS: m/z 389 [M(35Cl)+H]+, Rt 3.29 min.

Aufarbeitung

  1. additionwas added
  2. temperaturebefore being cooled
  3. filtrationfiltered
  4. washThe solid was washed with DCM
  5. washthe filtrate washed with sat. NaHCO3
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe title compound was precipitated from a DCM/i-Pr2O mixture
  10. filtrationfiltered
  11. concentrationThe filtrate was then concentrated
  12. custompurified by flash chromatography (DCM/MeOH: 98/2)
  13. customto afford another batch of product

Quellen und Nachweise

ORD-Eintrag
ord-4f3f923fdb354641981c26f97768e553
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09023842B2

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