4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → HCID 86628923, compound

HRID 1919454Notes

Reaction equation

HRID 1919454 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:27])([CH3:26])[C@@H:14]([O:18][Si:19]([CH3:25])([CH3:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C:15]([OH:17])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2].Br[CH2:29][C:30]1[O:34][C:33](=[O:35])[O:32][C:31]=1[CH3:36]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:27])([CH3:26])[C@@H:14]([O:18][Si:19]([CH3:25])([CH3:24])[C:20]([CH3:21])([CH3:23])[CH3:22])[C:15]([O:17][CH2:36][C:31]1[O:32][C:33](=[O:35])[O:34][C:30]=1[CH3:29])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-oneHCID 86628885HCID 86628885, compound

Product 1

HCID 86628923HCID 86628923, compoundYield 5.3%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

Following the general procedure for the preparation of acyloxyalkyl/alkoxycarbonyloxyalkyl carboxylic esters from carboxylic acids of Description 22, (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)butanoic acid (19) (1.5 g, 3.5 mmol) dissolved in 15 mL of anhydrous toluene was reacted with 1.4 g (7.0 mmol) of commercially available 5-bromomethyl-4-methyl-1,3-dioxolen-2-one in the presence of 1.4 g (5.3 mmol) of silver carbonate (Ag2CO3). After work-up and further purification by mass-guided preparative HPLC, 0.1 g (5.3% yield) of the title compound (48a) was obtained as a colorless, viscous oil. Rf=0.62 (EtOAc/MeOH=19:1). MS (ESI) m/z 538.14 (M+H)+, 560.13 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter work-up and further purification by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-5d799dd0353140198e58b9d948c18293
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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