Methyl chloroformate → Boc-DTrp(COOMe)-OBzl

HRID 1196737

Reaktionsgleichung

Reaktionsgleichung von HRID 1196737
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[OH-].[Na+].Cl[C:33]([O:35][CH3:36])=[O:34]>ClCCl.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:33]([O:35][CH3:36])=[O:34])[CH:5]=1

Komponenten

6

Edukt 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 10739405Boc-DTrp-OBzl

Produkt 1

HCID 10813513Boc-DTrp(COOMe)-OBzlAusbeute 123,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of Boc-DTrp-OBzl(1 g) in dichloromethane(8 ml) was added Bu4NHSO4 (8.62 mg) and pulverized NaOH(253 mg) under ice cooling. To the resulting suspension was added dropwise a solution of methyl chloroformate(599 mg) in dichloromethane(6 ml) under ice cooling over a period of 30 min. The reaction mixture was stirred under ice cooling for 30 min and at room temperature for 12 h, diluted with dichloromethane, washed successively with water, 5% KHSO., saturated NaHCO3 and saturated NaCl, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to give Boc-DTrp(COOCH3)-OBzl(1.42 g) as a colorless solid. The solid was hydrogenolized over a catalytic amount of 10% Pd/C in methanol under an atmosphere of hydrogen(under atmospheric pressure) to give Boc-DTrp(COOCH3).

Aufarbeitung

  1. washwashed successively with water, 5% KHSO
  2. dry with material, saturated NaHCO3 and saturated NaCl, dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dbdcf614e9dd4c529c992f2a6ada03a6
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05114918

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