4-Iodo-1,2-dimethylbenzene → (s)-n-(3,4-Dimethyl-phenyl)-2-hydroxy-2-phenyl-n-(2-thiophen-3-yl-ethyl)-acetamide

HRID 1094415Notes

Reaction equation

HRID 1094415 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][NH2:8])=[CH:2]1.I[C:10]1[CH:11]=[C:12]([CH3:17])[C:13]([CH3:16])=[CH:14][CH:15]=1.C([O:21][C:22](=O)[C@H:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[OH:24])(=O)C>>[CH3:17][C:12]1[CH:11]=[C:10]([N:8]([CH2:7][CH2:6][C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[C:22](=[O:21])[C@@H:23]([OH:24])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:15]=[CH:14][C:13]=1[CH3:16]

Participants

4

Reactant 3

HCID 1416464-Iodo-1,2-dimethylbenzeneHCID 122587372-(3-Thienyl)ethanamineHCID 87431886acetyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 58007551(s)-n-(3,4-Dimethyl-phenyl)-2-hydroxy-2-phenyl-n-(2-thiophen-3-yl-ethyl)-acetamide

Procedure

In analogy to example 22 step 1 and 26 step 1-2, (3,4-dimethyl-phenyl)-(2-thiophen-3-yl-ethyl)-amine obtained by reacting 2-thiophen-3-yl-ethylamine (commercial) with 4-iodo-o-xylene (commercial) was coupled with (S)-(+)-O-acetyl-L-mandelic acid then hydrolysed to provide the title compound. MS(m/e): 366.2 [M+H]+.

Sources & evidence

ORD record
ord-56b8f36f1dd14125877732f11e1648b8
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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