Imidazole → HCID 67073663, compound

HRID 454985Notes

Reaction equation

HRID 454985 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[NH:10][C@H:11]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[O:21][CH3:22])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26].N1C=CN=C1.CCOC(C)=O.O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:23])[NH:10][C@H:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][Si:28]([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29])=[CH:16][C:15]=1[O:21][CH3:22])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22728543Water ethylacetateHCID 67073707HCID 67073707, compound

Product 1

HCID 67073663HCID 67073663, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [(R)-2-hydroxy-1-(4-hydroxy-2-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester (736.3 mg, 2.32 mmol), TBSCl (840.2 mg, 5.57 mmol) and imidazole (757.2 mg, 11.1 mmol) in DCM was stirred at rt for 24 h. The reaction was worked up with EtOAc/H2O. Flash column provided the titled compound (585.7 mg, 59%).

Sources & evidence

ORD record
ord-cff9cc18393f464c8d9cc413c8903e49
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Reaction notes

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