Thiomorpholine → HCID 18659476, compound

HRID 275622Notes

Reaction equation

C([O:3][C:4]([CH:6]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:7][S:8]([C:11]([CH3:16])([CH3:15])[C:12](Cl)=[O:13])(=[O:10])=[O:9])=[O:5])C.[NH:24]1[CH2:29][CH2:28][S:27][CH2:26][CH2:25]1>>[CH3:15][C:11]([S:8]([CH2:7][C@@H:6]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:4]([OH:3])=[O:5])(=[O:9])=[O:10])([C:12]([N:24]1[CH2:29][CH2:28][S:27][CH2:26][CH2:25]1)=[O:13])[CH3:16]

Participants

Reactant 2

HCID 67164Thiomorpholine

HCID 20088424HCID 20088424, compound

Product 1

HCID 18659476HCID 18659476, compound

Procedure

In an analogous manner to that described in Example 1, paragraphs (d) and (e), starting from 2-mercaptoisobutyric acid and ethyl 2-benzylacrylate there was obtained (RS)-2-[[2-[(ethoxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride, reaction of which with thiomorpholine analogously to Example 2, paragraph (a), and subsequent enzymatic hydrolysis analogously to Example 6, paragraph (c), yielded (S)-α-[[[1-methyl-1-[(tetrahydro-4H-1,4-thiazin-4-yl)carbonyl]ethyl]sulfonyl]methyl]hydrocinnamic acid, MS: 399 (M)+, as a colourless solid.

Sources & evidence

ORD record: ord-464254a189924c169dc1d9de0cba694a
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05393875

Reaction notes

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