2-Butyne-1,4-diol → HCID 21304721, compound

HRID 2084963Notes

Reaction equation

HRID 2084963 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][S:14][C:13]([CH3:18])([CH3:17])[C@@H:12]2[C:19]([O:21][CH3:22])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:23](O)[C:24]#[C:25][CH2:26][OH:27]>>[OH:27][CH2:26][C:25]#[C:24][CH2:23][O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][S:14][C:13]([CH3:17])([CH3:18])[C@@H:12]2[C:19]([O:21][CH3:22])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80662-Butyne-1,4-diolHCID 57020974HCID 57020974, compound

Product 1

HCID 21304721HCID 21304721, compoundYield 65.2%

Procedure

According to the procedure of Step 2 of Example 248, Mitsunobu coupling of 0.10 g (0.288 mmoL) of methyl(3S)-4-[(4-hydroxyphenyl)sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxylate and 0.031 g (0.363 mmol) of 2-butyne-1,4-diol gave 0.078 g of methyl(3S)-4-({4-[(4-hydroxy-2-butynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholine carboxylate as a colorless oil.

Sources & evidence

ORD record
ord-3a5117b507ea4e29a0db9c074145c8b9
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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