2,2,5-trimethyl-1,3-dioxane-5-carboxylic Acid → HCID 23513806, compound

HRID 353560Notes

Reaction equation

C(O[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=[O:5])C.[CH3:27][C:28]1([CH3:38])[O:33][CH2:32][C:31]([CH3:37])(C(O)=O)[CH2:30][O:29]1>>[CH2:23]([O:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([CH2:12][C:9]2([C:28]([O:29][CH2:30][CH3:31])=[O:33])[CH2:10][CH2:11][N:6]([C:4]([C:31]3([CH3:37])[CH2:30][O:29][C:28]([CH3:27])([CH3:38])[O:33][CH2:32]3)=[O:5])[CH2:7][CH2:8]2)(=[O:14])=[O:15])=[CH:21][CH:20]=1)[C:24]#[C:25][CH3:26]

Participants

Reactant 2

HCID 113557762,2,5-trimethyl-1,3-dioxane-5-carboxylic Acid

HCID 69911783HCID 69911783, compound

Product 1

HCID 23513806HCID 23513806, compoundYield 131.8%

Procedure

Ethyl 4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-1-[(2,2,5-trimethyl-1,3-dioxan 5-yl)carbonyl]-4-piperidinecarboxylate was prepared according to the general method as outlined in Example 30 (step 8). Starting from 4-[[[4-(2-Butynyloxy)phenyl]sulfonyl]methyl]piperidinecarboxylic acid ethyl ester (0.333 g, 0.8 mmol) and 2,2,5-trimethyl-(1,3)dioxane-5-carboxylic acid (0.168 g, 0.96 mmol), 0.339 g (79%) of the desired product was isolated as a white solid. Electrospray Mass Spec: 536.1 (M+H)+.

Workup

customEthyl 4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-1-[(2,2,5-trimethyl-1,3-dioxan 5-yl)carbonyl]-4-piperidinecarboxylate was prepared

Sources & evidence

ORD record: ord-807b74ec61c740bf80afa159cfa07c96
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06753337B2

Reaction notes

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