Trimethylamine → HCID 86746909, compound

HRID 1587149Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][P:5]([OH:40])([O:7][C@@H:8]([CH3:39])[C:9]([O:11][C@H:12]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:38])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:13]1)=[O:10])=[O:6].[CH3:41][N:42]([CH3:44])[CH3:43]>C1(C)C=CC=CC=1>[OH-:4].[CH3:27][CH:26]([CH2:25][CH2:24][CH2:23][C@H:22]([C@@H:21]1[C@:30]2([CH3:38])[C@H:18]([C@H:17]3[C@H:33]([CH2:32][CH2:31]2)[C@:34]2([CH3:37])[C:14]([CH2:13][C@@H:12]([O:11][C:9]([C@@H:8]([O:7][P:5]([OH:40])([O:4][CH2:3][CH2:2][N+:42]([CH3:44])([CH3:43])[CH3:41])=[O:6])[CH3:39])=[O:10])[CH2:36][CH2:35]2)=[CH:15][CH2:16]3)[CH2:19][CH2:20]1)[CH3:29])[CH3:28]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 0.7 g of cholest-5-en-3β-yl (S)-2-[[(2-bromoethoxy)hydroxyphosphinyl]oxy]propionate in 15 ml of toluene is treated with 15 ml of trimethylamine in a dry-ice bath. The mixture is heated to 60° C. for 30 hours. After cooling the reaction mixture is taken up in toluene and concentrated. The residue is taken up in 30 ml of methanol, treated with 2 g of silver carbonate and stirred at 50° C. for 0.5 hour. The precipitate is filtered off, concentrated and there is obtained 0.6 g of O-[[(S)-1-[(cholest-5-en-3β-yloxy)carbonyl]ethoxy]hydroxyphosphinyl]choline hydroxide internal salt, MS: 624 (M+H+).

Workup

temperatureAfter cooling the reaction mixture
concentrationconcentrated
additiontreated with 2 g of silver carbonate
filtrationThe precipitate is filtered off
concentrationconcentrated

Sources & evidence

ORD record: ord-2d084de03a004968b0005be89b1335a7
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05215972

Reaction notes

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