Diglycolamine → HCID 86748489, compound

HRID 275624Notes

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](O)=[O:13])(=[O:10])=[O:9])=[O:5])C.[NH2:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][OH:30]>>[OH:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][NH:24][C:12]([C:11]([S:8]([CH2:7][CH:6]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:4]([OH:5])=[O:3])(=[O:10])=[O:9])([CH3:16])[CH3:15])=[O:13]

Participants

Reactant 2

HCID 13578Diglycolamine

HCID 20088445HCID 20088445, compound

Product 1

HCID 86748489HCID 86748489, compound

Procedure

In an analogous manner to that described in Example 6, paragraphs (a) to (c), starting from 2-mercaptoisobutyric acid and ethyl 2-benzylacrylate there was obtained (RS)-2-[[2-[(ethoxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionic acid, reaction of which 2-(2-aminoethoxy)ethanol and subsequent enzymatic hydrolysis of the resulting ethyl ester yielded (S/R=9/1 )-α-[[[1-[[2-(2-hydroxyethoxy)ethyl]carbamoyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamic acid, MS: 401.9 (M+H)+, as a colourless oil.

Sources & evidence

ORD record: ord-d895567b41624699a3696294a581b748
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05393875

Reaction notes

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