Sodium Methoxide → HCID 71271219, compound

HRID 335494Notes

Reaction equation

HRID 335494 reaction equation
C([O:4][C@@H:5]1[C@@H:13]([CH2:14][O:15]C(=O)C)[O:12][C@H:11]2[C@H:7]([N:8]=[C:9]([NH:19][C:20](=[O:24])/[CH:21]=[CH:22]/[CH3:23])[S:10]2)[C@H:6]1[O:25]C(=O)C)(=O)C.C[O-].[Na+]>CO>[OH:4][C@@H:5]1[C@@H:13]([CH2:14][OH:15])[O:12][C@H:11]2[C@H:7]([N:8]=[C:9]([NH:19][C:20](=[O:24])/[CH:21]=[CH:22]/[CH3:23])[S:10]2)[C@H:6]1[OH:25]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86731576HCID 86731576, compound

Product 1

HCID 71271219HCID 71271219, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 10 mL reaction vial was added (3aR,5R,6S,7R,7aR)-5-[(acetyloxy)methyl]-2-[(2E)-but-2-enoylamino]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diyl diacetate (40.00 mg; 0.10 mmol; 1.00 eq.) in methanol (2.00 ml) followed by sodium methanolate (0.00 ml; 0.01 mmol; 0.10 eq.). The obtained clear solution was stirred at room temperature for 1 h. LCMS showed a strong peak of SM plus desired product and byproduct (m/z=331). After 5 h, LMCS only showed the product's peak. The solution was diluted with 10 mL MeOH before it was transferred into a 50 mL round-bottom flask. Half spoon resin (Dowex 50WX8) was added. The mixture was gently stirred for 10 sec before it was filtered. 30 mL MeOH was used to rinsed the cake. The obtained solution was concentrated and lyophilized to afford 90.6% of the title compound as a white solid.

Workup

  1. customTo a 10 mL reaction

Sources & evidence

ORD record
ord-bb687ace56104288bdab3d247f09b303
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

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