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4-Methylmorpholine → 4-(tert-Butyl-dimethyl-silanyloxy)-3-({7-[(naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carbonyl}-amino)-butyric Acid Benzyl Ester

HRID 722746
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 722746
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][CH:14]1[C:21](=[O:22])[N:20]2[CH:23]([C:27](O)=[O:28])[CH2:24][CH2:25][CH2:26][CH:19]2[CH2:18][CH:17]=[CH:16][CH2:15]1)=[O:12].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.ON1C2C=CC=CC=2N=N1.[CH2:59]([O:66][C:67](=[O:80])[CH2:68][CH:69]([NH2:79])[CH2:70][O:71][Si:72]([C:75]([CH3:78])([CH3:77])[CH3:76])([CH3:74])[CH3:73])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>C1COCC1.O>[CH2:59]([O:66][C:67](=[O:80])[CH2:68][CH:69]([NH:79][C:27]([CH:23]1[N:20]2[C:21](=[O:22])[CH:14]([NH:13][C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[O:12])[CH2:15][CH:16]=[CH:17][CH2:18][CH:19]2[CH2:26][CH2:25][CH2:24]1)=[O:28])[CH2:70][O:71][Si:72]([C:75]([CH3:76])([CH3:77])[CH3:78])([CH3:74])[CH3:73])[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1
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Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23571419HCID 23571419, VerbindungHCID 696597087-[(Naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid

Produkt 1

HCID 69659665
4-(tert-Butyl-dimethyl-silanyloxy)-3-({7-[(naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carbonyl}-amino)-butyric Acid Benzyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

7-[(Naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid (0.44 gm) is dissolved in 15 mL THF to which 0.24 gm of 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC), 0.15 mL of N-methylmorpholine, and 0.17 gm of 1-hydroxybenzotriazole (HOBt) is added. The reaction mixture is stirred for 20 min then added to a solution of 3-amino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid benzyl ester (0.52 gm, prepared by methods described in Chem. Pharm. Bull. 1999, 47, 11–21) in 5 mL THF. The resulting mixture is striired at RT for ˜18 h, then poured into water, and extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, then dried over sodium sulfate powder. Filtration and evaporation produces a crude product which is then purified over silica (1:1 ethylacetate:hexanes) to afford the desired product.

Aufarbeitung

  1. additionis added
  2. waitThe resulting mixture is striired at RT for ˜18 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate powder
  6. filtrationFiltration and evaporation
  7. customproduces a crude product which
  8. customis then purified over silica (1:1 ethylacetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2b1d0af5ccaa4ae79d8240acc45d9a0e
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07138395B2

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