Cesium carbonate → HCID 77699942, compound

HRID 1174060Notes

Reaction equation

HRID 1174060 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[C@@H:12]1[C@:17]2([C:25]3[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:27])[C@H:16]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[CH2:15][C:14](=[O:35])[NH:13]1)[CH:2]=[CH2:3].[CH3:36][O:37][CH:38]([Si:40]([CH3:43])([CH3:42])[CH3:41])[CH3:39].[C:44]([O:48][C:49](=[O:52])[CH2:50]Br)([CH3:47])([CH3:46])[CH3:45].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[CH:12]1[C:17]2([C:25]3[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:27])[CH:16]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[CH2:15][C:14](=[O:35])[N:13]1[CH2:50][C:49]([O:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:52])[CH:2]=[CH2:3].[CH3:36][O:37][CH:38]([Si:40]([CH3:43])([CH3:42])[CH3:41])[CH3:39]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 69276711HCID 69276711, compound

Product 1

HCID 77699942HCID 77699942, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in example 1e, racemic (2′R, 3R,4′S)-2′-(2-allyloxy-5-iodo-phenyl)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-2,6′-dioxo spiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (5 g, 6.6 mmol) prepared in example 18c was reacted with bromo-acetic acid tert-butyl ester and cesium carbonate in N,N-dimethyl-formamide to give racemic (2′R, 3R, 4′S)-2′-(2-allyloxy-5-iodo-phenyl)-1′-[(tert-butoxycarbonyl)methyl]-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-2,6′-dioxo spiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a white foam (Yield: 2.8 g, 49%).

Sources & evidence

ORD record
ord-c021aea2961f44b78801a593f95dea63
Source dataset
uspto-grants-2010_11
Patent number
US07834179B2

Reaction notes

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