Methyl iodide → HCID 178488620, compound

HRID 339831Notes

Reaction equation

HRID 339831 reaction equation
[OH:1][CH2:2][CH2:3][C@H:4]([NH:11][C:12]1[O:13][C:14]([CH3:28])([CH3:27])[CH:15]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[S:16](=[O:19])(=[O:18])[N:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:29]C(C)([O-])C.[K+].CI>CN(C)C=O>[CH3:29][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH:15]2[C:14]([CH3:28])([CH3:27])[O:13][C:12]([NH:11][C@H:4]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:3][CH2:2][OH:1])=[N:17][S:16]2(=[O:18])=[O:19])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178431675HCID 178431675, compound

Product 1

HCID 178488620HCID 178488620, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 40 mg of 4-[2-((S)-3-hydroxy-1-phenylpropylamino)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-5-yl]phenol in 1 ml of N,N-dimethylformamide were added, at room temperature, 11 mg of potassium tert-butoxide and 28 mg of methyl iodide, and the reaction mixture was stirred at constant temperature for 3 hours. The reaction solution was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined and lyophilized. This gave the product (10 mg) with a molecular weight of 418.5 g/mol (C21H26N2O5S); MS (ESI): m/e=419 (M+H+).

Workup

  1. customThe reaction solution was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-f433b5fcfce64c84acc73149a69b9e09
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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