Реакция #66020

ord-2f778455cdc94321a61a4a298bb79c4b

Уравнение реакции

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(Br)cc2)cc1
4-(4-bromophenoxy)-benzenesulphonyl chloride
O=S(=O)(Cl)c1ccc(Oc2ccc(Br)cc2)cc1
4-(4-Bromo-phenoxy)-benzenesulphonyl chloride
→
CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(Oc2ccc(Br)cc2)cc1
Compound 4d
CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(Oc2ccc(Br)cc2)cc1
{[4-(4-Bromophenoxy)-benzenesulphonyl]-tert-butoxycarbonylmethyl-amino}-aceticacid tert-butyl ester

Реактанты

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(Br)cc2)cc1
4-(4-bromophenoxy)-benzenesulphonyl chloride
O=S(=O)(Cl)c1ccc(Oc2ccc(Br)cc2)cc1
4-(4-Bromo-phenoxy)-benzenesulphonyl chloride

Реагенты

Нет

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Методика

Compound 4d was prepared similar to the procedure described for 4a using 4-(4-bromophenoxy)-benzenesulphonyl chloride (3d) (3.00 g, 8.63 mmol). Yield: 4.13 g, 7.42 mmol, 86% (light yellow solid). 1H NMR (DMSO-d6): δ 7.70 (d, J=8.2 Hz, 2H, ArH), 7.52 (d, J=8.8 Hz, 2H, ArH), 7.01 (d, 3J=8.8 Hz, 2H, ArH), 6.67 (d, 3J=8.9 Hz, 2H, ArH) 4.05 (s, 4H, 2×CH2CO2 tBu), 1.46 (s, 18H, 2×CO2tBu).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08524194B2uspto-grants-2013_09