Trimethylsilyldiazomethane → HCID 46229265, compound

HRID 46198Notes

Reaction equation

HRID 46198 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[S:21][C:22]([OH:25])=[N:23][N:24]=1.[CH3:26][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[S:21][C:22]([O:25][CH3:26])=[N:23][N:24]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178521057HCID 178521057, compound

Product 1

HCID 46229265HCID 46229265, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-hydroxy-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol (100 mg, 0.26 mmol) from step 2 in dichloromethane (8 mL) and methanol (2 mL) at 0° C. was added (trimethylsilyl)diazomethane (2.0 M in diethyl ether, 0.65 mL, 1.3 mmol). The reaction mixture was stirred with gradual warming to ambient temperature over 1 h and concentrated in vacuo. Purification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient) provided the title compound (69 mg, 0.17 mmol, 66%) as a yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient)

Sources & evidence

ORD record
ord-09b1f4c501744a08b2b32e55dcf01f1d
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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