1,2-Dichloroethane → HCID 86585259, Verbindung

HRID 2117023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2117023
C([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([I:18])[CH:12]=1)(OC(C)(C)C)=O.[C:22](OC(=O)C)(=[O:24])C.[CH2:29](Cl)[CH2:30]Cl.C1C=CC2N([OH:42])N=NC=2C=1.[NH3:43].C(O)(=O)[CH2:45][C:46]([CH2:51]C(O)=O)([C:48](O)=O)[OH:47]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.CC(O)C>[C:22]([NH:43][C:19](=[O:21])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:29](=[O:42])[CH3:30])=[C:13]([I:18])[CH:12]=1)[NH2:8])([O:47][C:46]([CH3:45])([CH3:48])[CH3:51])=[O:24]

Komponenten

10

Edukt 6

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 311Citric AcidHCID 7918Acetic AnhydrideHCID 757711-HydroxybenzotriazoleHCID 15545208N-(tert-Butoxycarbonyl)-3-iodo-L-tyrosine

Produkt 1

HCID 86585259HCID 86585259, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a solution of N-Boc-3-iodotyrosine (0.380 g, 0.93 mmol) in pyridine (1 mL) were added acetic anhydride (105 μL, 1.1 mmol) and DMAP (10 mg, cat). The solution was stirred 1.5 h then diluted in 5% citric acid (20 mL), and the product extracted with EtOAc. The organic solution was evaporated and the residue dissolved in MeCN (4 mL). To the stirred cold (ice bath) solution were added EDC (0.196 g, 1.0 mmol) and HOBt (0.135 g, 1.0 mmol). After stirring for 1 h, a 2 N solution of ammonia in iPrOH (3 mL) was added. The suspension was stirred 1 h at 5° C., the solid was filtered, the filtrate evaporated and the residue purified by flash chromatography (gradient 3-5% MeOH/chloroform) to yield N-Boc-O-acety-3-iodotyrosine amide.

Aufarbeitung

  1. extractionthe product extracted with EtOAc
  2. customThe organic solution was evaporated
  3. dissolutionthe residue dissolved in MeCN (4 mL)
  4. stirringAfter stirring for 1 h
  5. stirringThe suspension was stirred 1 h at 5° C.
  6. filtrationthe solid was filtered
  7. customthe filtrate evaporated
  8. customthe residue purified by flash chromatography (gradient 3-5% MeOH/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-aef00f7278c043519ffcc928edc33f0d
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439258B2

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