tert-Butylsulfinamide, (S)-(-)- → HCID 71171587, compound

HRID 1829905Notes

Reaction equation

HRID 1829905 reaction equation
C([S@@](N)=O)(C)(C)C.[C:8]1([C@@H:14]([O:28][S@@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])[C@@H:15]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH3:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:8]1([C@H:14]([O:28][S@:29]([C:31]([CH3:32])([CH3:34])[CH3:33])=[O:30])[C@H:15]([NH:17][S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])[CH3:16])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86605457HCID 86605457, compound

Product 1

HCID 71171587HCID 71171587, compoundYield 86%

Procedure

Preparation of (S)-t-butyl sulfinamide from (S)-2-Methyl-2-propylsulfinic acid (1R,2S)-1-phenyl-2-(4-toluenesulfonylamino)-propyl ester: The same procedure described above was followed, an furnished the title product in 86% yield and 96% ee. (HPLC, Chiralpak AS column, 90:10 hexane/ethanol; 1.2 mL/min, 222 nm; (R)-TBSA rt=6.6 min; (S)-TBSA, rt=9.4 min.). 1H NMR(CDCl3): δ 1.18 (s, 9H), 3.82 (br, s, 2H). 13C NMR (CDCl3): δ 22.1, 55.3.

Sources & evidence

ORD record
ord-c225e7187fde4115be02678ac5fb197e
Source dataset
uspto-grants-2006_06
Patent number
US07064214B2

Reaction notes

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