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Triethylamine → (2-Methoxyethoxy)methyl-2-{[1-({[(3s)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1h-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric acid

HRID 32355
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 32355
[C:1]([O:5][C:6](=[O:40])[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C@H:10]([NH:19][C:20]([C:22]2([CH2:27][CH:28]([CH2:32][C:33]([NH:35][CH:36]([CH3:38])[CH3:37])=[O:34])[C:29]([OH:31])=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[C:9]1=[O:39])([CH3:4])([CH3:3])[CH3:2].[CH3:41][O:42][CH2:43][CH2:44][O:45][CH2:46]Cl.C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:41][O:42][CH2:43][CH2:44][O:45][CH2:46][C:28]([CH2:27][C:22]1([C:20]([NH:19][C@H:10]2[CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]([CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:40])[C:9]2=[O:39])=[O:21])[CH2:26][CH2:25][CH2:24][CH2:23]1)([CH2:32][C:33]([NH:35][CH:36]([CH3:37])[CH3:38])=[O:34])[C:29]([OH:31])=[O:30]
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 589354242-{[1-({[(3S)-1-(2-tert. butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric Acid

Produkt 1

HCID 69272815(2-Methoxyethoxy)methyl-2-{[1-({[(3s)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1h-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

300 mg 2-{[1-({[(3S)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric acid (for preparation see Example 12) was dissolved in 5 ml dichloromethane. 33 mg DMAP, 74 μl methoxyethoxymethyl chloride and 90 μl triethylamine were added to this receiving solution. The reaction mixture was stirred overnight, then diluted with 5 ml dichloromethane and the organic phase was washed in succession once each with 3 ml dilute aqueous KHSO4 solution and saturated aqueous common salt solution. The organic phase was dried over magnesium sulfate, the solvent was largely evaporated at reduced pressure and the remaining residue was chromatographed on silica gel (mobile phase: EA/cyclohexane 2:1 v/v). Drying the product fractions in an oil pump vacuum yielded 191 g of the title compound, MS: [M+H]+: 646; m/z: 590, 540, 484, 425.

Aufarbeitung

  1. washthe organic phase was washed in succession once each with 3 ml dilute aqueous KHSO4 solution and saturated aqueous common salt solution
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was largely evaporated at reduced pressure
  4. customthe remaining residue was chromatographed on silica gel (mobile phase: EA/cyclohexane 2:1 v/v)
  5. customDrying the product fractions in an oil pump vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8a6b5cd84c4a4679bc4fa08bef6346bc
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07427611B2

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