Ethanol → HCID 51002954, compound

HRID 389329Notes

Reaction equation

HRID 389329 reaction equation
[C:1]([S@@:5]([NH:7][C@H:8]([C:12]1([C:17]([O:19]CC)=O)[S:16][CH2:15][CH2:14][S:13]1)[CH2:9][CH2:10][CH3:11])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:22][NH2:23].C(O)C>>[C:1]([S@@:5]([NH:7][C@H:8]([C:12]1([C:17]([NH:23][CH3:22])=[O:19])[S:16][CH2:15][CH2:14][S:13]1)[CH2:9][CH2:10][CH3:11])=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 51002902HCID 51002902, compound

Product 1

HCID 51002954HCID 51002954, compoundYield 98%

Procedure

A heavy-walled glass tube was charged with ethyl (S,SS)-2-[1-(tert-butylsulfinylamino)butyl]-1,3-dithiolane-2-carboxylate (0.50 g, 1.4 mmol) and a chilled 8.0 M solution of methylamine in ethanol (5 mL, 40 mmol). The mixture was allowed to warm to room temperature and was allowed to stand for 72 hours. Distillation of the solvent at reduced pressure afforded (S,SS)-2-[1-(tert-butylsulfinylamino)butyl]-N-methyl-1,3-dithiolane-2-carboxamide (0.47 g, 98%) as a viscous amber-colored oil.

Workup

  1. distillationDistillation of the solvent at reduced pressure

Sources & evidence

ORD record
ord-f6b9fc89e41c4e82ae0c527b053f9427
Source dataset
uspto-grants-2013_02
Patent number
US08378124B2

Reaction notes

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