Cysteamine → HCID 22592849, compound

HRID 1290697Notes

Reaction equation

HRID 1290697 reaction equation
Br[CH:2]([CH2:10]Br)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[SH:12][CH2:13][CH2:14][NH2:15].C(N(CC)CC)C.C(Cl)(Cl)Cl>C1C=CC=CC=1>[S:12]1[CH2:13][CH2:14][NH:15][CH:2]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:10]1

Participants

6

Reactant 4

HCID 6058CysteamineHCID 6212ChloroformHCID 8471TriethylamineHCID 54532549855-41-6

Product 1

HCID 22592849HCID 22592849, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Preferably, t-butyl 2,3-dibromopropionate prepared according to J. Perkin Trans I, p. 1321 (1973) is treated with 2-mercaptoethylamine and triethylamine in a suitable solvent, such as a mixture of chloroform and benzene, to provide t-butyl tetrahydro-2H-1,4-thiazine-3-carboxylate, which upon reaction with a compound of the formula V under suitable conditions, such as in the presence of triethylamine in dichloromethane solution at 25° C., provides compounds of the formula II-c. Oxidation of this material with a suitable oxidizer, such as sodium perborate or m-chloroperbenzoic acid, provides the corresponding sulfoxide, preferably as a single diastereomer.

Sources & evidence

ORD record
ord-5f3e20ce42644712b981f5ff5c7e84b2
Source dataset
uspto-grants-1998_05
Patent number
US05753653

Reaction notes

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