HCID 22480908, compound → HCID 86583709, compound

HRID 1279894Notes

Reaction equation

HRID 1279894 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][C:4](=[O:19])[CH2:5][C@@H:6]([CH2:16][CH:17]=[CH2:18])[C:7]([NH:9][CH:10]([CH2:14][OH:15])[C:11]([O-:13])=[O:12])=O.Cl.[CH2:23](N(CC)CC)[CH3:24].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>O1CCCC1>[CH3:21][C:2]([CH3:1])([CH3:20])[CH2:3][C:4](=[O:19])[CH2:5][C@H:6]([C:7]1[O:15][CH2:14][C@@H:10]([C:11]([O:13][CH2:23][CH3:24])=[O:12])[N:9]=1)[CH2:16][CH:17]=[CH2:18]

Participants

4

Reactant 2

HCID 22480908HCID 22480908, compoundHCID 131723482HCID 131723482, compound

Product 1

HCID 86583709HCID 86583709, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl (2S)-2-{[(2R)-2-(4,4-dimethyl-2-oxopentyl)-4-pentenoyl]amino-3-hydroxypropanoate (Preparation 113) (23.8 g, 72.3 mmol) in anhydrous tetrahydrofuran (300 ml), under a nitrogen atmosphere, was treated with (methoxycarbonylsulfamoyl)triethylammonium hydroxide triethylamine hydrochloride salt (43.5 g, 79.4 mmol) and stirred at reflux for 1.5 hours. After allowing to cool to room temperature the mixture was filtered, washed with ethyl acetate and the filtrate was concentrated under reduced pressure. The oil was purified by column chromatography on silica gel eluting with a solvent gradient of 80:20 (hexane:diethylether) gradually changing to 50:50 (hexane:diethylether) to afford the title compound as a colourless oil (11.0 g).

Workup

  1. temperatureat reflux for 1.5 hours
  2. filtrationwas filtered
  3. washwashed with ethyl acetate
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe oil was purified by column chromatography on silica gel eluting with a solvent gradient of 80:20 (hexane:diethylether)

Sources & evidence

ORD record
ord-626a425b8ee64172a36bc9281f4a7c38
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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