2-Butyne-1,4-diol → HCID 21304726, compound

HRID 1976489Notes

Reaction equation

HRID 1976489 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][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:26](O)[C:27]#[C:28][CH2:29][OH:30]>>[OH:30][CH2:29][C:28]#[C:27][CH2:26][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][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80662-Butyne-1,4-diolHCID 11552805HCID 11552805, compound

Product 1

HCID 21304726HCID 21304726, compoundYield 48.2%

Procedure

According to the procedure of Step 2 of Example 248, Mitsunobu coupling of 2.5 g (6.46 mmol) of tert-butyl (3S)-4-[(4-hydroxyphenyl)sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxylate and 0.667 g (7.752 mmol) of 2-butyne-1,4-diol gave 1.42 g of tert-butyl (3 S)-4-({4-[(4-hydroxy-2-butynyl)oxy]phenyl)sulfonyl)-2,2-dimethyl-3-thiomorpholine carboxylate as a colorless oil.

Sources & evidence

ORD record
ord-c4b75d193d084410aac7ce6f3053a835
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

Loading…