3-Phenyl-2-propyn-1-ol → HCID 57134211, compound

HRID 2084955Notes

Reaction equation

HRID 2084955 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].[C:23]1([C:29]#[C:30][CH2:31]O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH3:11][C:10]1([CH3:12])[S:9][CH2:8][CH2:7][N:6]([S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:31][C:30]#[C:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)(=[O:15])=[O:14])[C@H:5]1[C:3]([O:2][CH3:1])=[O:4]

Participants

3

Reactant 2

HCID 1231153-Phenyl-2-propyn-1-olHCID 227319314-(4-Hydroxy-benzenesulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid methyl ester

Product 1

HCID 57134211HCID 57134211, compoundYield 55.3%

Procedure

According to the procedure of Step 2 of Example 248, Mitsunobu coupling of 0.345 g (1.0 mmol) of 4-(4-hydroxy-benzenesulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid methyl ester and 0.159 g (1.2 mmol) of 3-phenyl-2-propyn-1-ol provided 0.254 g (55%) of methyl(3S)-2,2-dimethyl-4-({4-[(3-phenyl-2-propynyl)oxy]phenyl}sulfonyl)-3-thiomorpholine carboxylate as a pale yellow solid.

Sources & evidence

ORD record
ord-95fb55b3557947be82a3d0c83782cfcd
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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