Lithium Chloride → (S)-N-(1-((tert-butyldiphenylsilyl)oxy)-3-chloropropan-2-yl)methane-sulfonamide

HRID 524360Notes

Reaction equation

[Si:1]([O:18][CH2:19][C@@H:20]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:21]CS([O-])(=O)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-:32].[Li+]>CN(C=O)C.C(OCC)(=O)C>[Si:1]([O:18][CH2:19][C@H:20]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:21][Cl:32])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 250 mL three neck flask fitted with a thermometer, condenser, stirbar, under argon was added the bis-methanesulfonyl derivative 6 (44 g, 0.091 mol) dissolved in DMF (200 mL). Lithium chloride (5.8 g, 0.136 mol) was added in one portion. The reaction mixture was heated to 80° C. with an oil bath. After 90 min the reaction was allowed to cool to room temperature and diluted with 50% ethyl acetate in hexanes (880 mL). The layers were separated and the organic layer was washed with water (2×550 mL) and brine (550 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to 35 g (90%) of the chlorosulfonamide 7 as a yellow viscous oil. HPLC analysis showed a purity of 95%. 1H NMR (300 MHz, CDCl3) δ 7.3-7.7 (m, 10H), 4.6-4.8 (m, 1H), 3.6-4.0 (m, 5H), 2.9 (s, 3H), 1.1 (s, 9H).

Workup

temperatureto cool to room temperature
customThe layers were separated
washthe organic layer was washed with water (2×550 mL) and brine (550 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure to 35 g (90%) of the chlorosulfonamide 7 as a yellow viscous oil

Sources & evidence

ORD record: ord-912411b1964f4ca69742f156a6587a4b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340534B2

Reaction notes

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