Triethylamine → thiacycline

HRID 2398439Notes

Reaction equation

HRID 2398439 reaction equation
[CH3:1][N:2]([CH3:31])[CH:3]1[CH:20]2[C:7]([OH:25])([C:8]([OH:24])=[C:9]3[CH:18]([CH2:19]2)[S:17][C:16]2[C:11](=[C:12]([OH:22])[CH:13]=[CH:14][C:15]=2Cl)[C:10]3=[O:23])[C:6](=[O:26])[C:5]([C:27]([NH2:29])=[O:28])=[C:4]1[OH:30].C(N(CC)CC)C>CO>[CH3:31][N:2]([C@@H:3]1[C:4](=[O:30])[C:5]([C:27]([NH2:29])=[O:28])=[C:6]([OH:26])[C@:7]2([OH:25])[C@H:20]1[CH2:19][C@@H:18]1[S:17][C:16]3[C:11](=[C:12]([OH:22])[CH:13]=[CH:14][CH:15]=3)[C:10]([OH:23])=[C:9]1[C:8]2=[O:24])[CH3:1]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 178482997HCID 178482997, compound

Product 1

HCID 54676882thiacycline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

467 mg of 7-chloro-6-thiatetracycline in 25 ml of methanol are hydrogenated in the presence of 101 mg of triethylamine on 200 mg of 10% Pd-on-charcoal at 20° and normal pressure to give 6-thiatetracycline.

Sources & evidence

ORD record
ord-f3ec6552c23244cb9e6e699c65b2e1da
Source dataset
uspto-grants-1977_05
Patent number
US04024272

Reaction notes

Loading…