Tetrahydropyranyl ether → HCID 57047881, compound

HRID 2084964Notes

Reaction equation

O1CCCCC1OC1CCCCO1.[CH3:14][C:15]1([CH3:52])[S:20][CH2:19][CH2:18][N:17]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]#[C:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38]C3CCCCO3)=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C@H:16]1[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46]>>[OH:38][CH2:37][CH2:36][CH2:35][CH2:34][C:33]#[C:32][CH2:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([S:21]([N:17]2[CH2:18][CH2:19][S:20][C:15]([CH3:52])([CH3:14])[C@@H:16]2[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

Reactant 2

HCID 263182Tetrahydropyranyl ether

HCID 57286747HCID 57286747, compound

Product 1

HCID 57047881HCID 57047881, compoundYield 84%

Procedure

According to the procedure of Step 1 of Example 245 the tetrahydropyranyl ether of 0.659 g (1.13 mmol) of tert-butyl(3S)-2,2-dimethyl-4-[(4-{[7-(tetrahydro-2H-pyran-2-yloxy)-2-heptynyl]oxy}phenyl)sulfonyl]-3-thiomorpholinecarboxylate was cleaved to provide 0.472 g (84%) of tert-butyl(3S)-4-({4-[(7-hydroxy-2-heptynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholinecarboxylate as a colorless oil. Electrospray Mass Spec: 498.3 (M+H)+.

Sources & evidence

ORD record: ord-8bc156fce4ee49f69e8a119538783625
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716833B2

Reaction notes

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