Cesium carbonate → {[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]carbonyl}methyl N-methyl-N-[(phenylmethoxy)carbonyl]glycinate

HRID 1356437Notes

Reaction equation

HRID 1356437 reaction equation
[C:1]([N:11]([CH2:13][C:14]([OH:16])=[O:15])[CH3:12])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:17][C:18]([C:21]1[CH:22]=[C:23]([C:32](=[O:35])[CH2:33]Br)[CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])([CH3:20])[CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:12][N:11]([C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])[CH2:13][C:14]([O:16][CH2:33][C:32]([C:23]1[CH:24]=[C:25]([C:28]([CH3:30])([CH3:29])[CH3:31])[C:26]([OH:27])=[C:21]([C:18]([CH3:20])([CH3:19])[CH3:17])[CH:22]=1)=[O:35])=[O:15]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 97053N-CarbobenzoxysarcosineHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one

Product 1

HCID 22987727{[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]carbonyl}methyl N-methyl-N-[(phenylmethoxy)carbonyl]glycinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This intermediate is obtained in a standard fashion starting from Cbz-Sarcosine and 1-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2-bromo-ethanone in the presence of caesium carbonate in DMF.

Workup

  1. customThis intermediate is obtained in a standard fashion

Sources & evidence

ORD record
ord-8ff1809601ff457889813c5a2b229d0f
Source dataset
uspto-grants-2003_07
Patent number
US06586454B2

Reaction notes

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