Phenylmethanesulfonyl chloride → HCID 178427609, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of D-Arg(Tos)-Gly-OBn (5.2 mmol; Boc previously removed by treatment with 40% TFA/DCM (0.1M) for 15 min. and then concentrated in vacuo; RP-HPLC: 13.8 min.; C18, 0-100% CH3CN over 25 min., 1.5 mL/min) in 21 mL of DCM is neutralized with DIEA before cooling to −78° C. where 1.19 g (6.24 mmol) of BnSO2Cl is added as a solid followed by 900 uL (10.4 mmol). The solution is allowed to warm to 23° C. and stirr for 18 h. The eaction mixture was extracted twice with 10% citric acid, twice with 5% NaHCO3 (50 mL), brine (50 mL), dried (MgSO4), and concentrated in vacuo to give 3.2 g (97%) of BnSO2-D-Arg(Tos)Gly-OBn as a white solid. RP-HPLC: 18.0 min.;C18, 0-100% CH3CN over 25 min., 1.5 mL/min.

Provenance & Evidence