Acetyl chloride → HCID 66700204, compound

HRID 1717210Notes

Reaction equation

HRID 1717210 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:20][CH2:19][C@:18]3([CH2:24][CH2:23][NH:22][C:21]3=[O:25])[N:17]2C(OC(C)(C)C)=O)=[CH:12][CH:11]=1.C([Cl:36])(=O)C>CCOC(C)=O.CO>[ClH:36].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C@H:16]2[CH2:20][CH2:19][C@:18]3([CH2:24][CH2:23][NH:22][C:21]3=[O:25])[NH:17]2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 58027442HCID 58027442, compound

Product 1

HCID 66700204HCID 66700204, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,1-dimethylethyl (2R,5R)-2-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (D26, 29.3 g) in AcOEt (325 mL) and MeOH (108 mL) at 0° C., was added acetyl chloride (28.5 mL). The resulting solution was stirred at 0° C. for 15 minutes then at ambient temperature for 16 hours. Solvent was evaporated (bath temperature: first ambient and then 38° C.) and the residue solid was triturated with Et2O (3×244 mL). Finally the solid was collected by filtration and dried under high vacuum at 35° C. overnight to afford the title compound (23 g, Y=92%) as white solid.

Workup

  1. waitat ambient temperature for 16 hours
  2. customSolvent was evaporated (bath temperature
  3. customfirst ambient and then 38° C.) and the residue solid was triturated with Et2O (3×244 mL)
  4. filtrationFinally the solid was collected by filtration
  5. customdried under high vacuum at 35° C. overnight

Sources & evidence

ORD record
ord-e38e39a72a5e45f2bd23e21d915c481f
Source dataset
uspto-grants-2010_09
Patent number
US07803833B2

Reaction notes

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