Imidazole → HCID 67313854, compound

HRID 1010706Notes

Reaction equation

HRID 1010706 reaction equation
CN(C=O)C.[CH2:6]([O:8][C:9](=[O:23])[C@H:10]1[CH2:14][C@H:13]([OH:15])[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:7].[C:24]([Si:28]([CH3:31])([CH3:30])Cl)([CH3:27])([CH3:26])[CH3:25].N1C=CN=C1>CCOCC>[CH2:6]([O:8][C:9](=[O:23])[C@H:10]1[CH2:14][C@H:13]([O:15][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:31])[CH3:30])[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 12709317HCID 12709317, compound

Product 1

HCID 67313854HCID 67313854, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

12.2 Under an argon atmosphere, 120 ml of DMF are added to 28.01 g of 1-tert-butyloxycarbonyl-(2R,4S)-4-hydroxyproline ethyl ester, 30.28 g of tert-butyldimethylchlorosilane and 16.41 g of imidazole. The mixture is stirred for a further 2 hours. MTB ether is added, and the mixture is subjected to conventional work-up. The residue is chromatographed on silica gel, giving 40.4 g of 1-tert-butyloxycarbonyl-(2R,4S)-4-(tert-butyldimethylsilyl-oxy)proline ethyl ester as an oil.

Workup

  1. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-6ea549ff5af941d8bed45f8a7bbb627c
Source dataset
uspto-grants-2011_07
Patent number
US07977343B2

Reaction notes

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