Acetyl chloride → HCID 86598348, compound

HRID 1268764Notes

Reaction equation

HRID 1268764 reaction equation
C(C1C=C[C:6]([C@:9]23[CH2:35][C:25]4([NH:29][C@H:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:27][S:26]4)[CH2:24][N:10]2[C:11](=[O:23])[N:12]([C:15]2C=C(Cl)C=C(Cl)C=2)[C:13]3=[O:14])=[CH:5]C=1)#N.[C:36](Cl)(=[O:38])[CH3:37]>C(#N)C>[C:36]([N:29]1[C@@H:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:27][S:26][C:25]21[CH2:24][N:10]1[C:11](=[O:23])[N:12]([CH3:15])[C:13](=[O:14])[C@:9]1([CH2:6][CH3:5])[CH2:35]2)(=[O:38])[CH3:37]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86598349HCID 86598349, compound

Product 1

HCID 86598348HCID 86598348, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl (4′R,7aS)-7a-(4-cyanophenyl)-2-(3,5-dichlorophenyl)-1,3-dioxotetrahydro-1H-spiro[pyrrolo[1,2-c]imidazole-6,2′-[1,3]thiazolidine]-4′-carboxylate (examples 12–13, crude mixture of isomers, 0.30 g, 0.58 mmol) and ET3N (0.10 ml, 0.6 mmol)) in acetonitrile (3 mL) was added acetyl chloride (0.05 ml) and the contents stirred one night at RT. The reaction mixture was concentrated under reduced pressure and partitioned between dichloromethane (25 mL) and 1N Hydrochloric acid (10 mL). The dichloromethane layer was washed with 1N Sodium Bicarbonate, water then dried over sodium sulfate, concentrated and purified by silica gel chromatography using cyclohexane/ethyl acetate as the eluent, diluted with t-butyl methyl ether, washed with water, NaHCO3 solution, water then dried over sodium sulfate, concentrated and purified by silica gel chromatography using dichloromethane/acetone as the eluent. yield: 0.016 g. 1H NMR (CDCl3): 7.6 (2H, d), 7.35 (2H, d), 7.3 (1H, m), 6.8 (2H, m), 4.9 (1H, m), 4.75 (1H, d), 4.3 (2H, q), 4.05 (1H, d), 3.5–3.2 (5H, m), 2.65 (1H, d), 2.15 (3H, s), 1.3 (3H, t).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompartitioned between dichloromethane (25 mL) and 1N Hydrochloric acid (10 mL)
  3. washThe dichloromethane layer was washed with 1N Sodium Bicarbonate, water
  4. dry with materialthen dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography
  7. additiondiluted with t-butyl methyl ether
  8. washwashed with water, NaHCO3 solution, water
  9. dry with materialthen dried over sodium sulfate
  10. concentrationconcentrated
  11. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3c470a629a1345ea9bc92e0e5c365921
Source dataset
uspto-grants-2007_04
Patent number
US07199125B2

Reaction notes

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