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Phosgene → 1-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 1445422
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1445422
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].[C:27]([O-:30])(O)=O.[Na+].C(Cl)(Cl)=O.[CH2:36]([NH:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)[CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:22])[CH3:21])[CH2:16][N:15]2[C:27](=[O:30])[N:43]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 57956448Hept-6-enyl-(4-methoxy-benzyl)-amineHCID 686756681-{[4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Produkt 1

HCID 68675874
1-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester
Ausbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Compound 124 (5.88 g, 15.4 mmol) was dissolved in THF (200 ml), NaHCO3 (s) (appr. 10 ml) was added followed by phosgene-solution (20% in toluene, 15.9 ml, 30.7 mmol). The reaction mixture was stirred vigorously for 1 h and then filtrated, evaporated and redissolved in DCM (200 ml). NaHCO3 (s) (appr. 10 ml) was added followed by hept-6-enyl-(4-methoxy-benzyl)-amine (5.58 g, 23.9 mmol). The reaction mixture was stirred at room temperature overnight, filtrated and evaporated on silica. The crude product was purified by column chromatography on silica (EtOAc/n-Heptane 25/75-50/50) to give the title compound (4.9 g, 50%).

Aufarbeitung

  1. filtrationfiltrated
  2. customevaporated
  3. dissolutionredissolved in DCM (200 ml)
  4. additionNaHCO3 (s) (appr. 10 ml) was added
  5. stirringThe reaction mixture was stirred at room temperature overnight
  6. filtrationfiltrated
  7. customevaporated on silica
  8. customThe crude product was purified by column chromatography on silica (EtOAc/n-Heptane 25/75-50/50)

Quellen und Nachweise

ORD-Eintrag
ord-271cd91e78094bc9810efc0300140e51
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07666834B2

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