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Diisopropylethylamine → (3s)-3-(Benzo[1,3]dioxol-5-yl)-3-((5-(2-methoxycarbonyl-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester

HRID 413219
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 413219
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=1)=[O:4].[C:15]([O:19][C:20](=[O:33])[CH2:21][C@H:22]([NH2:32])[C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=1)([CH3:18])([CH3:17])[CH3:16].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(C(C)C)CC)(C)C>CN(C)C=O.ClCCl>[C:15]([O:19][C:20](=[O:33])[CH2:21][C@@H:22]([C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=1)[NH:32][C:12]([C:10]1[S:11][C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:8][CH:9]=1)=[O:14])([CH3:18])([CH3:16])[CH3:17]
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Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 108676335-(2-Methoxycarbonyl-ethyl)-thiophene-2-carboxylic acidHCID 57048399tert-butyl (3S)-3-amino-3-(1,3-dioxaindan-5-yl)propanoate

Produkt 1

HCID 57125533
(3s)-3-(Benzo[1,3]dioxol-5-yl)-3-((5-(2-methoxycarbonyl-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester
Ausbeute 130 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

214 mg (1 mmol) of 5-(2-methoxycarbonyl-ethyl)-thiophene-2-carboxylic acid (example 1, step b) were dissolved in 5 ml of anhydrous dimethylformamide. 265 mg (1 mmol) of (3S)-3-amino-3-(benzo[1,3]dioxol-5-yl)-propionic acid tert-butyl ester and 328 mg (1 mmol) of TOTU were added, and 3 mmol (0.51 ml) of N,N-diisopropyl-N-ethylamine were added to keep the pH of the mixture at 7.5 to 8. The reaction mixture was stirred for 4.5 hours at room temperature. Solvents were removed under reduced pressure to give a dark brown oil. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution, 10% citric acid and with water. Then the organic phase was dried with anhydrous magnesium sulfate. After filtration the solvents were removed in vacuo to give 600 mg of a brownish oil which was purified by chromatography (silica gel; ethyl acetate/heptane (1/2, v/v)). 425 mg of a resin were obtained.

Aufarbeitung

  1. customSolvents were removed under reduced pressure
  2. customto give a dark brown oil
  3. washwashed with saturated sodium bicarbonate solution, 10% citric acid and with water
  4. dry with materialThen the organic phase was dried with anhydrous magnesium sulfate
  5. filtrationAfter filtration the solvents
  6. customwere removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b23099658e441fbb2daa8415733d4e2
Quelldatensatz
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06566366B1

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