2-Methyl-2-butene → HCID 86648539, compound

HRID 43529Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21]([CH:23]=[O:24])[N:22]=3)[CH2:14][C@H:13]2[O:30][CH2:31][CH2:32][CH3:33])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl([O-])=[O:35].[Na+].P([O-])(O)(O)=O.[Na+].CC(=CC)C>>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21]([C:23]([OH:35])=[O:24])[N:22]=3)[CH2:14][C@H:13]2[O:30][CH2:31][CH2:32][CH3:33])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

Reactant 4

HCID 105532-Methyl-2-butene

HCID 23668197Sodium Chlorite

HCID 23672064Monosodium phosphate

HCID 86648540HCID 86648540, compound

Product 1

HCID 86648539HCID 86648539, compoundYield 97.4%

Procedure

The same operation as in Example (33c) was performed using ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-propoxypiperidin-1-yl)-4-formyl-1,3-thiazole-5-carboxylate obtained in Example (74b) (445 mg, 0.89 mmol), sodium chlorite (180 mg, 1.99 mmol), sodium dihydrogenphosphate (557.6 mg, 3.57 mmol) and 2-methyl-2-butene (0.57 mL, 5.36 mmol), to obtain 445.4 mg of the title compound as a white solid (97%).

Sources & evidence

ORD record: ord-4569c92715254744bc65617329f990fe
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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