4-Benzyloxy-2-butyn-1-ol → Methyl 4-[(4-{[(benzyloxy)-2-butynyl]oxy)phenyl}-sulfonyl]-2,2-dimethyl-3-thiomorpholine carboxylate

HRID 2414655Notes

Reaction equation

HRID 2414655 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:10]([CH3:12])([CH3:11])[S:9][CH2:8][CH2:7][N:6]1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])=[O:4].[CH2:23]([O:30][CH2:31][C:32]#[C:33][CH2:34]O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([O:30][CH2:31][C:32]#[C:33][CH2:34][O:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([N:6]2[CH2:7][CH2:8][S:9][C:10]([CH3:12])([CH3:11])[CH:5]2[C:3]([O:2][CH3:1])=[O:4])(=[O:15])=[O:14])=[CH:21][CH:20]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 110303484-Benzyloxy-2-butyn-1-olHCID 227319314-(4-Hydroxy-benzenesulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid methyl ester

Product 1

HCID 22644829Methyl 4-[(4-{[(benzyloxy)-2-butynyl]oxy)phenyl}-sulfonyl]-2,2-dimethyl-3-thiomorpholine carboxylateYield 42%

Procedure

According to the procedure of Step 4 of Example 243, Mitsunobu coupling of 0.345 g (1.0 mmol) of 4-(4-hydroxy-benzenesulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid methyl ester and 0.211 g (1.2 mmol) of 4-(benzyloxy)-2-butyn-1-ol provided 0.211 g (42%) of methyl 4-[(4-{[4-(benzyloxy)-2-butynyl]oxy}phenyl)sulfonyl]-2,2-dimethyl-3-thiomorpholine carboxylate as a pale yellow oil.

Sources & evidence

ORD record
ord-e27a2f0ded454192a735da67ab9c8b2f
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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