Reaction #51756

ord-4785ced226c74426bde033d537ae8572

Reaction equation

CC(C)(C)OC(=O)N1CCc2cc(SC#N)c(C(C)(C)C)cc21
6-tert-butyl-5-thiocyanato-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester
O[C@H](CS)[C@H](O)CS
dithiothreitol
O=P([O-])([O-])[O-]
phosphate
→
CC(C)(C)OC(=O)N1CCc2cc(S)c(C(C)(C)C)cc21
title compound
CC(C)(C)OC(=O)N1CCc2cc(S)c(C(C)(C)C)cc21
6-tert-Butyl-5-mercapto-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Reactants

CC(C)(C)OC(=O)N1CCc2cc(SC#N)c(C(C)(C)C)cc21
6-tert-butyl-5-thiocyanato-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester
O[C@H](CS)[C@H](O)CS
dithiothreitol
O=P([O-])([O-])[O-]
phosphate

Reagents

None

Solvents

CCO
EtOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe crude product was used without any purification

Procedure

The title compound was prepared according to General Method 14 using 6-tert-butyl-5-thiocyanato-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (prepared in Example KK; 2.0 g, 6.6 mmol), dithiothreitol (1.21 g, 7.9 mmol), EtOH (100 mL), and phosphate buffer (pH: 7.5, 10 mL). The crude product was used without any purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06852711B2uspto-grants-2005_02