Lithium iodide → HCID 57142506, compound

HRID 2084966Notes

Reaction equation

[I-].[Li+].[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([N:24]2[CH2:29][CH2:28][S:27][C:26]([CH3:31])([CH3:30])[C@@H:25]2[C:32]([O:34]C(C)(C)C)=[O:33])(=[O:23])=[O:22])=[CH:17][CH:16]=1)(=[O:5])[CH3:4]>>[C:3]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([N:24]2[CH2:29][CH2:28][S:27][C:26]([CH3:30])([CH3:31])[C@@H:25]2[C:32]([OH:34])=[O:33])(=[O:22])=[O:23])=[CH:19][CH:20]=1)(=[O:5])[CH3:4]

Participants

Reactant 2

HCID 66321Lithium iodide

HCID 57254020HCID 57254020, compound

Product 1

HCID 57142506HCID 57142506, compoundYield 100.1%

Procedure

According to the procedure of Example 251, lithium iodide mediated ester cleavage of 0.456 g (0.845 mmol) of tert-butyl(3S)-4-[(4-{[7-(acetyloxy)-2-heptynyl]-oxy}phenyl)sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxylate provided 0.409 g (100%) of (3S)-4-[(4-{[7-(acetyloxy)-2-heptynyl]oxy)phenyl)sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxylic acid as a colorless oil. Electrospray Mass Spec: 446.0 (M+H)+.

Sources & evidence

ORD record: ord-4f27894160f9474ebb5a040a82286842
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716833B2

Reaction notes

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