alpha Lipoic acid → 5-[1,2]Dithiolan-3-yl-pentanoic acid [4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-yl]-amide

HRID 457884Notes

Reaction equation

HRID 457884 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[S:2]1.[CH3:13][C:14]1[N:15]=[C:16]([NH2:25])[S:17][C:18]=1[CH2:19][CH2:20][O:21][N+:22]([O-:24])=[O:23]>>[CH3:13][C:14]1[N:15]=[C:16]([NH:25][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH:3]2[CH2:4][CH2:5][S:1][S:2]2)[S:17][C:18]=1[CH2:19][CH2:20][O:21][N+:22]([O-:24])=[O:23]

Participants

3

Reactant 2

HCID 864alpha Lipoic acidHCID 115574994-Methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine

Product 1

HCID 588203185-[1,2]Dithiolan-3-yl-pentanoic acid [4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-yl]-amideYield 51%

Procedure

Pet-151 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using 5-[1,2]Dithiolan-3-yl-pentanoic acid (DL-Lipoic acid) and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 51% as a pale yellow liquid.

Workup

  1. customPet-151 was prepared
  2. customthe procedure described above for the preparation of Pet-154

Sources & evidence

ORD record
ord-c10f534efc344681872df91a854fb452
Source dataset
uspto-grants-2007_03
Patent number
US07189750B2

Reaction notes

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