4-Toluenesulfonyl chloride → HCID 71534086, compound

HRID 1670667Notes

Reaction equation

CN(C=O)C.CS(C)=O.[S:10](Cl)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[CH3:21][O:22][C:23](=[O:38])[C@H:24]([CH2:36][OH:37])[NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].C(N(CC)CC)C>CN(C=O)C>[CH2:29]([O:28][C:26]([NH:25]/[C:24](=[CH:36]\[O:37][S:10]([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11])/[C:23]([O:22][CH3:21])=[O:38])=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a pre-cooled (−30° C.) solution of DMF:DMSO (1:1, 200 mL) under nitrogen was added TsCl (76.3 g, 0.4 mol) in small portions over 30 min. NOTE: This reaction is highly exotermic and careful temperature control is essential! The solution was stirred at −10° C. for 10 min, then again taken to −30° C. A solution of cbz-L-serine methyl ester (20.3 g, 0.08 mol, CAS 1676-81-9) in DMF was added dropwise, again with careful temperature control. After stirring for 10 min at −30° C. triethylamine (110 mL, 0.79 mol) was added and the reaction was slowly taken to 0° C. and kept at this temperature for 2 h. The reaction was quenched by addition of ice-cold water. The solution was extracted with 3×EtOAc, then the combined organic layer was washed extensively with brine and water. Drying and evaporation gave product as yellow oil (30 g, 94%).

Workup

customagain taken to −30° C
additionwas added
customwas slowly taken to 0° C.
waitkept at this temperature for 2 h
customThe reaction was quenched by addition of ice-cold water
extractionThe solution was extracted with 3×EtOAc
washthe combined organic layer was washed extensively with brine and water
customDrying
customevaporation

Sources & evidence

ORD record: ord-313ffdb48a8f4dffa8b7750654b8c4ea
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994179B2

Reaction notes

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