Propargyl alcohol → HCID 21304724, compound

HRID 2414664Notes

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

Participants

Reactant 2

HCID 7859Propargyl alcohol

HCID 11552805HCID 11552805, compound

Product 1

HCID 21304724HCID 21304724, compoundYield 95%

Procedure

According to the procedure of Step 2 of Example 248, Mitsunobu coupling of 0.30 g (0.775 mmoL) of tert-butyl (3S)-4-[(4-hydroxyphenyl)sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxylate and 0.054 mL (0.93 mmol) of propargyl alcohol gave 0.313 g of tert-butyl (3S)-2,2-dimethyl-4-{[4-(2-propynyloxy)phenyl]sulfonyl}-3-thiomorpholine carboxylate as a white solid. Electrospray Mass Spec 426.4 (M+H)+

Sources & evidence

ORD record: ord-b41ec66b086840829e873776b1a93d29
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812227B2

Reaction notes

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