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Triethylamine → 2-((1S)-1-tert-Butoxycarbonyl-2-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-ethylsulfamoyl)-benzoic acid methyl ester

HRID 427317
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 427317
[C:1]([O:5][C:6](=[O:25])[C@@H:7]([NH2:24])[CH2:8][NH:9][C:10](=[O:23])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:33][O:34][C:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43](Cl)(=[O:45])=[O:44])=[O:36]>CN(C)C=O>[CH3:33][O:34][C:35](=[O:36])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43](=[O:44])(=[O:45])[NH:24][C@H:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:25])[CH2:8][NH:9][C:10](=[O:23])[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:16]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 15550489(2S)-2-Amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl ester

Produkt 1

HCID 570397222-((1S)-1-tert-Butoxycarbonyl-2-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-ethylsulfamoyl)-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

0.123 g (0.35 mmol) of (2S)-2-amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl ester was dissolved in 2 ml of dimethylformamide and treated with 0.196 ml (1.4 mmol) of triethylamine and 0.164 g (0.7 mmol) of 2-(methoxycarbonyl)-benzenesulfonyl chloride. The solution was stirred for 4 hours at room temperature. The solvent was removed in vacuo, the residue was dissolved in dichloromethane and the solution was washed three times with water. The organic phase was dried with sodium sulfate, filtered and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (1/1). Yield 75 mg. MS (ES+): m/e=549 (M+H+).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washthe solution was washed three times with water
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (1/1)

Quellen und Nachweise

ORD-Eintrag
ord-bdb23bccba614a7c9936f7b315095ae0
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06313119B1

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