Acetyl chloride → HCID 57908090, compound

HRID 1013083Notes

Reaction equation

HRID 1013083 reaction equation
[NH2:1][CH2:2][C:3]1[NH:7][C:6](=[O:8])[C:5]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[N:4]=1.CCN(CC)CC.[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl>[C:28]([NH:1][CH2:2][C:3]1[NH:7][C:6](=[O:8])[C:5]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[N:4]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57908096HCID 57908096, compound

Product 1

HCID 57908090HCID 57908090, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(aminomethyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-ene-8-carboxylate (1E) in CH2Cl2 (150 mg, 0.05 M), prepared by the procedure of Example 1, was added Et3N and acetyl chloride at −45° C. The reaction was complete after 20 minutes at −30° C. as determined by LCMS analysis, and then partitioned between ethyl acetate and water. The organics were subsequently washed with NaHCO3 and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was passed thorough a pad of silica to afford the tert-butyl 2-(acetamidomethyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-ene-8-carboxylate (2A, 87%).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organics were subsequently washed with NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a219f5a5c5c4080bba29d8b7780f6f5
Source dataset
uspto-grants-2011_07
Patent number
US07981904B2

Reaction notes

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