Methyl iodide → (3aR,5S,6S,7R,7aR)-2-[ethyl(methyl)amino]-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-5-carboxylic acid

HRID 335492Notes

Reaction equation

HRID 335492 reaction equation
[CH2:1]([NH:3][C:4]1[S:5][C@H:6]2[O:12][C@H:11]([C:13]([OH:15])=[O:14])[C@@H:10]([OH:16])[C@H:9]([OH:17])[C@H:7]2[N:8]=1)[CH3:2].[C:18](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH2:1]([N:3]([CH3:18])[C:4]1[S:5][C@H:6]2[O:12][C@H:11]([C:13]([OH:15])=[O:14])[C@@H:10]([OH:16])[C@H:9]([OH:17])[C@H:7]2[N:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71271091CID 71271091

Product 1

HCID 71271038(3aR,5S,6S,7R,7aR)-2-[ethyl(methyl)amino]-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 5 mL sure seal vial was added (3aR,5S,6S,7R,7aR)-2-(ethylamino)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-5-carboxylic acid (53.00 mg; 0.20 mmol; 1.00 eq.) in N,N-dimethylformamide (2.00 ml) followed by dipotassium carbonate (55.85 mg; 0.40 mmol; 2.00 eq.) and iodomethane (29.69 μl; 0.40 mmol; 2.00 eq.). The mixture was stirred at room temperature for overnight before it was concentrated, purified by Yamazen C1 (40 g column, 220 nm) and dried with lyophilize to afford 7.3 mg (9.3%) monomethylated compound as white solid and two sets of peaks were found on NMR, ratio=3:1.

Workup

  1. concentrationwas concentrated
  2. custompurified by Yamazen C1 (40 g column, 220 nm)
  3. customdried with lyophilize
  4. customto afford 7.3 mg (9.3%)

Sources & evidence

ORD record
ord-96d7a776658e44ca9ead7233b918cc49
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

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