L-Tartaric acid → HCID 86649829, compound

HRID 625901Notes

Reaction equation

[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH3:11][C@@H:12]([NH:22][CH2:23][C@H:24]([OH:35])[C:25]1[CH:26]=[CH:27][C:28]([OH:34])=[C:29]([NH:31][CH:32]=[O:33])[CH:30]=1)[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1.NC1C=C([C@@H](O)CN[C@H](C)CC2C=CC(OC)=CC=2)C=CC=1O>CO>[CH3:11][C@@H:12]([NH:22][CH2:23][C@H:24]([OH:35])[C:25]1[CH:26]=[CH:27][C:28]([OH:34])=[C:29]([NH:31][CH:32]=[O:33])[CH:30]=1)[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1.[C:6]([C@@H:4]([C@H:2]([C:1]([O-:10])=[O:9])[OH:3])[OH:5])([O-:8])=[O:7]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution containing 3.9 g (26 mmol) of L-tartaric acid and 36 mL of methanol was added to a solution of 9 g (26 mmol) of arformoterol base and 144 mL methanol at 23° C. Afterwards, the resulting mixture was seeded with form D and stirred at 23° C. for 1 hour. It was then further cooled to 0-5° C. for 1 hour and the product collected by filtration and dried under inlet air (atmospheric pressure) for 16 hours to provide 11.1 g (86% yield) (99.7% chemical purity, containing 0.14% of the degradation impurity (R)-1-(3-amino-4-hydroxyphenyl)-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethanol) of (R,R)-formoterol L-tartrate form D, as an off white powder. 1H-NMR (200 MHz, d6-DMSO) δ: 1.03 (d, 3H); 2.50-2.67 (m, 5H); 3.72 (s, 3H); 3.99 (s, 2H); 4.65-4.85 (m, 1H); 6.82-7.15 (m, 5H); 8.02 (s, 1H); 8.28 (s, 1H); 9.60 (s, NH). No residual solvent was detected (1H-NMR).

Workup

temperatureIt was then further cooled to 0-5° C. for 1 hour
filtrationthe product collected by filtration
customdried under inlet air (atmospheric pressure) for 16 hours
customto provide 11.1 g (86% yield) (99.7% chemical purity

Sources & evidence

ORD record: ord-2b0a5827d2124d50ad88438e685051d8
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309186B2

Reaction notes

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