Triethylamine → tert-Butyl 4(S)-(2(S)-methanesulphonyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 507833Notes

Reaction equation

[OH:1][CH2:2][C@H:3]([CH:19]([CH3:21])[CH3:20])[CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH3:29][S:30]([O:1][CH2:2][C@H:3]([CH:19]([CH3:21])[CH3:20])[CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:32])=[O:31]

Participants

Conditions

Temperature: 0 °C

Procedure

The solution of 2.84 g of tert-butyl 4(S)-(2(S)-hydroxymethyl-3-methylbutyl)-2,2-dimethyl-oxazolidine-3-carboxylate in 100 ml of dichloromethane is admixed at 0° C. successively with 1.41 ml of triethylamine and 0.76 ml of methanesulphonyl chloride. The reaction mixture is stirred at 0° C. over 1 hour and subsequently concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly yellowish oil. Rf=0.30 (1:2 EtOAc-heptane); Rt=5.03 (gradient I).

Workup

concentrationsubsequently concentrated by evaporation

Sources & evidence

ORD record: ord-167742edac0e44c3b8862183be4590c1
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786307B2

Reaction notes

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