[(1S,2S)-2-isocyanatocyclohexyl]oxymethylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (109 mg, 0.49 mmol) and the crude (1S,2S)-(−)-2-benzyloxycyclohexyl isocynate in 2 mL of N,N-dimethyl-formamide was stirred at room temperature for 20 hours. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (60 mg, 27% two steps). LC-MS (m/z) 454.0 (M+). Purification upon Gilson HPLC eluting with acetonitrile/water (10/90, v/v to 90/10

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (109 mg, 0.49 mmol) and the crude (1S,2S)-(−)-2-benzyloxycyclohexyl isocynate in 2 mL of N,N-dimethyl-formamide was stirred at room temperature for 20 hours. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (60 mg, 27% two steps). LC-MS (m/z) 454.0 (M+). Purification upon Gilson HPLC eluting with acetonitrile/water (10/90, v/v to 90/10