Reaktion #66021

ord-87fee97c66ee4f39bed4407aa0680954

Reaktionsgleichung

CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(Oc2ccccc2)cc1
4a
CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(Oc2ccccc2)cc1
{[4-Phenoxy-benzenesulphonyl]-tert-butoxycarbonylmethyl-amino}-aceticacid tert-butyl ester
O=S(=O)(Cl)c1ccc(Oc2ccc(I)cc2)cc1
material 3e
O=S(=O)(Cl)c1ccc(Oc2ccc(I)cc2)cc1
4-(4-Iodo-phenoxy)-benzenesulfonyl chloride
→
CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(Oc2ccc(I)cc2)cc1
Compound 4e
CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(Oc2ccc(I)cc2)cc1
{[4-(4-Iodo-phenoxy)-benzenesulphonyl]-tert-butoxycarbonylmethyl-amino}-aceticacid tert-butyl ester

Edukte

CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(Oc2ccccc2)cc1
4a
CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(Oc2ccccc2)cc1
{[4-Phenoxy-benzenesulphonyl]-tert-butoxycarbonylmethyl-amino}-aceticacid tert-butyl ester
O=S(=O)(Cl)c1ccc(Oc2ccc(I)cc2)cc1
material 3e
O=S(=O)(Cl)c1ccc(Oc2ccc(I)cc2)cc1
4-(4-Iodo-phenoxy)-benzenesulfonyl chloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Compound 4e was prepared following the procedure described for 4a with reagent quantities adapted to the amount of starting material 3e (0.71 g, 1.81 mmol). Yield: 1.04 g, 1.64 mmol, 99% (white solid). 1H-NMR (DMSO-d6): δ 7.96 (d, 3J=8.5 Hz, 2H, ArH), 7.59 (d, 3J=8.5 Hz, 2H, ArH), 4.07 (s, 4H, 2×CH2CO2H), 1.40 (s, 18H, 2×CO2tBu).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524194B2uspto-grants-2013_09