Triacetoxyperiodinane → HCID 25011822, compound

HRID 1511475Notes

Reaction equation

HRID 1511475 reaction equation
[C:1]([NH:5][C:6](=[O:51])[NH:7][C@@H:8]([C:47]([CH3:50])([CH3:49])[CH3:48])[C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]2[C:18]3[CH:31]=[CH:30][S:29][C:19]=3[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:22]=2)[CH2:13][C@H:12]1[C:32]([NH:34][C@@H:35]([CH2:44][CH2:45][CH3:46])[CH:36]([OH:43])[C:37]([NH:39][CH:40]1[CH2:42][CH2:41]1)=[O:38])=[O:33])=[O:10])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([NH:5][C:6](=[O:51])[NH:7][C@@H:8]([C:47]([CH3:50])([CH3:49])[CH3:48])[C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]2[C:18]3[CH:31]=[CH:30][S:29][C:19]=3[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:22]=2)[CH2:13][C@H:12]1[C:32]([NH:34][C@@H:35]([CH2:44][CH2:45][CH3:46])[C:36](=[O:43])[C:37]([NH:39][CH:40]1[CH2:41][CH2:42]1)=[O:38])=[O:33])=[O:10])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57818278HCID 57818278, compound

Product 1

HCID 25011822HCID 25011822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-N-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)-4-(2-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4-yloxy)pyrrolidine-2-carboxamide (61) (1 mmol) was oxidized with Dess-Martin periodinane (1.2 mmol) in dry dichloromethane, to provide (2S,4R)-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)-4-(2-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4-yloxy)pyrrolidine-2-carboxamide (62) after aqueous/organic work up and purification of the crude product using silica gel chromatography.

Sources & evidence

ORD record
ord-fe72a26f2d564a17aa368a49a43cda70
Source dataset
uspto-grants-2012_07
Patent number
US08211897B2

Reaction notes

Loading…